ライフサイエンスコーパス: oxetane

1 H-bond-donor (HBD) catalyst to the activated oxetane.

2 on of a carbonyl with an alkene to afford an oxetane.

3 comes were influenced by substituents on the oxetane.

4 ing the formation of either an epoxide or an oxetane.

5 cyclization of a tosylate led to a bicyclic oxetane.

6 cluding without cleavage of the incorporated oxetane.

7 dic nucleophiles providing 2,2-disubstituted oxetanes.

8 riety of 3-substituted and 3,3-disubstituted oxetanes.

9 fluorine containing pyrazole derivatives and oxetanes.

10 cidic nucleophiles provide 2,2-disubstituted oxetanes.

11 se-constraining oxetane (OXE) modifications [oxetane, 1-(1',3'-O-anhydro-beta-d-psicofuranosyl nucleo

12 A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields,

13 Bromination of the polycyclic oxetane 2,4-oxytwistane (rac-(1R,3S,4R,7S,9R,11S)-2-oxat

14 Phosphoramidate prodrugs of a 2'-oxetane 2-amino-6-O-methyl-purine nucleoside demonstrate

15 ed photoredox hydrodecarboxylation of 2-aryl oxetane 2-carboxylic acids this work enables access to t

16 Chiral spirocyclic oxetanes [2-oxo-spiro(3H-indole-3,2'-oxetanes)] were sub

17 A six-step conversion of oxirane 3 to oxetane 9 is reported.

18 First, an oxetane acetal persists in concentrated mineral acid (1.

19 sition states were traced by considering the oxetane activation mode.

20 omosuccinimide (NBS)-mediated cyclization of oxetane alcohol 17, prepared from readily accessible 2-m

21 Aryl oxetane amines offer exciting potential as bioisosteres

22 Ten oxetane analogues of bioactive benzamides and marketed d

23 effective synthetic strategies to access new oxetane and azetidine derivatives and molecular scaffold

24 Oxetane and azetidine heterocyclic, -sulfoximine, and -p

25 Synthesis of bis-spiro-oxetane and bis-spiro-tetrahydrofuran pyrroline nitroxid

26 The mechanism for the coupling reaction of oxetane and carbon dioxide has been studied.

27 107.6 kJ x mol (-1) for copolymerization of oxetane and carbon dioxide supports this conclusion.

28 alytic systems for the selective coupling of oxetane and carbon dioxide to provide the corresponding

29 g reaction, and by the direct enchainment of oxetane and CO 2.

30 Moreover, aryl vinyl 1,3-diol/oxetane and indene ethanol readily reacted with the subs

31 Irida-oxetane and oxo-irida-allyl compounds are isolated, prod

32 is unexpected due to the ring strain of the oxetane and the anticipated facile ring opening retro-ox

33 sed to model the structure of the polycyclic oxetane and to assess the component of total ring strain

34 3-Aryl-3-carboxylic acid oxetanes and azetidines are suitable precursors to terti

35 Four-membered heterocycles such as oxetanes and azetidines represent attractive and emergen

36 lops a radical functionalization of benzylic oxetanes and azetidines using visible light photoredox c

37 ity of this method for construction of CF(3)-oxetanes and CF(3)-azetidines is illustrated by the form

38 ch is commonly employed for the synthesis of oxetanes and cyclobutanes, the synthesis of azetidines v

39 ctionalized 3-/4-aryl- and alkyl-substituted oxetanes and fused oxetane bicycles.

40 computational method DU8+, has revealed that oxetanes and related compounds constitute yet another si

41 ular Paterno-Buchi cyclization yielding endo-oxetanes and significantly changing the Cope-averaged NM

42 ed oxetanes by halides, including alkylidene oxetanes and spirocyclic oxetanes, was highly stereosele

43 thway for a set of more structurally diverse oxetanes and the degree of hydrolysis is modulated by mi

44 ycles, including 1,3-aminoalcohol, 1,3-diol, oxetane, and isoxazoline derivatives.

45 ms inclusively, the combinations of oxirane, oxetane, and tetrahydrofuran are rather extensive and co

46 od rate, and successfully enchains epoxides, oxetane, and/or tetrahydrofurans, providing a straightfo

47 ies relying on the formation of intermediate oxetanes, and protocols based on initial carbon-carbon b

48 hetic approach leverages novel cyclobutane-, oxetane-, and azetidine-substituted sulfonium salts, whi

49 ches to construct heterocyclic systems using oxetanes are described.

50 We have shown previously that oxetanes are hydrolyzed to diols by human microsomal epo

51 affolds such as cyclobutanes, azetidines and oxetanes are in high demand.

52 Oxetanes are strained heterocycles with unique propertie

53 Oxetanes are valuable intermediates in organic synthesis

54 Oxetanes are valuable motifs in medicinal chemistry appl

55 We intended to realize aryl vinyl oxetane as a 4pai-electrocyclization precursor to access

56 trategy was the reverse, i.e., to utilize an oxetane as the framework to construct the larger ring.

57 -conjugate addition producing a stable trans oxetane as the only regioisomer.

58 [2+2]-cycloaddition to form an intermediate oxetane as the turnover-limiting step.

59 Experimental evidence for oxetanes as reactive intermediates in the catalytic carb

60 are suitable precursors to tertiary benzylic oxetane/azetidine radicals which undergo conjugate addit

61 ycloaddition reaction of exocyclic arylidene oxetanes, azetidines, and cyclobutanes with simple elect

62 oxetane products are potential surrogates of oxetane, beta-lactone and carbonyl pharmacophores on the

63 yl- and alkyl-substituted oxetanes and fused oxetane bicycles.

64 ening can be directed toward the substituted oxetane by the addition of a Lewis acid.

65 actions for sulfonyl fluorides to form amino-oxetanes by an alternative pathway to the established Su

66 The ring-opening reaction of fluorinated oxetanes by halides, including alkylidene oxetanes and s

67 lective opening of enantiomerically enriched oxetanes by hydrogen peroxide, conversion of the resulti

68 t and a pyridine oxide, alkynyl oxiranes and oxetanes can be converted into functionalized five- or s

69 This study shows that oxetanes can be used as drug design elements for directi

70 A four-membered oxygen ring (oxetane) can be readily grafted into native peptides and

71 tational studies support the formation of an oxetane carbocation as the rate-determining step, follow

72 A defluorosulfonylation forms planar oxetane carbocations simply on warming.

73 ric ring-opening reaction of 3,3-substituted oxetanes catalyzed by chiral phosphoric acid (CPA) deriv

74 t to be characterized, it may enable general oxetane construction via oxa-conjugate addition.

75 developed the first synthesis of the unique oxetane containing diterpene (+)-dictyoxetane.

76 denosine 5'-phosphate to the dehydrogenated, oxetane containing precursor of oxetanocin A phosphate.

77 ted for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid.

78 ring and further derivatization of preformed oxetane-containing building blocks.

79 to understand the complete metabolic fate of oxetane-containing compounds, and further study is requi

80 Oxetane-containing ring systems are increasingly used in

81 he formation of the desired bond between the oxetane core and benzophenone derivatives, ultimately yi

82 The oxetane core is built using a Paterno-Buchi photochemica

83 e bases was modest, the triphosphate of a 2'-oxetane cytidine analogue demonstrated potent intrinsic

84 An oxetane D-ring has been fused to the framework of the hi

85 ring Taxol biobehavior as effectively as the oxetane D-ring.

86 istry are reported, including a collation of oxetane derivatives appearing in recent patents for medi

87 Finally, examples of oxetane derivatives in ring-opening and ring-expansion r

88 rview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the la

89 observed regioselectivity in the opening of oxetane derivatives.

90 n numerous studies into the synthesis of new oxetane derivatives.

91 rbonates prepared by the copolymerization of oxetanes derived from d-xylose with CO(2) and incorporat

92 a suitable chiral Bronsted acid catalyst, an oxetane desymmetrization by a well-positioned internal s

93 ectivity of chiral phosphoric acid-catalyzed oxetane desymmetrizations were investigated by density f

94 lene-functionalized 3-ethyl-3-(hydroxymethyl)oxetane (EAMO) repeat units (Patent No.: US 9,421,276) v

95 oselective desymmetrization of 3-substituted oxetanes enabled by a confined chiral phosphoric acid.

96 observed, which led to an enrichment of one oxetane enantiomer as the major enantiomer (15 examples,

97 he catalyst triplet by either one of the two oxetane enantiomers with a slight preference for the min

98 rs, which forms crosslinks with the reactive oxetane ends, thus repairing the network.

99 d D-seco derivatives, and structures with no oxetane equivalent underscores that the four-membered ri

100 on via classical C-C bond, and Paterno-Buchi oxetane formation followed or not by fragmentation (retr

101 Previous proposals suggested that oxetane formation follows the acetylation of taxadien-5a

102 zes an oxidative rearrangement in paclitaxel oxetane formation, which represents a previously unknown

103 sting state that undergoes a MLCT leading to oxetane formation.

104 hotocycloadditions are often typified by the oxetane-forming Paterno-Buchi reaction.

105 in interception have limited this attractive oxetane-forming pathway.

106 uces a new synthetic disconnection to access oxetanes from native alcohol substrates.

107 o characteristics considered responsible for oxetane function: (1) rigidification of the tetracyclic

108 The selective installation of the oxetane graft enhances stability and activity, as demons

109 Oxetane grafting of the genetically detoxified diphtheri

110 membered ring systems such as azetidines and oxetanes have been increasingly exploited as valuable sy

111 Oxetanes have garnered further interest as isosteres of

112 4-acetyl substituent is as important as the oxetane in determining the A ring conformation.

113 nd enabled access to the densely substituted oxetane in one step.

114 Examples of the use of oxetanes in medicinal chemistry are reported, including

115 cursors to the key intermediate, taxologenic oxetane, indicating the potential existence of multiple

116 and the N-methyl-3'T thietane analog of the oxetane intermediate.

117 thesis through a critical four-membered-ring oxetane intermediate.

118 Oxetane intermediates can be formed when C-C bond format

119 The oxetane is stable to acid and basic conditions, as are a

120 an intermediate en route to the synthesis of oxetane, is an equally potential precursor for the antic

121 The four-membered D-ring, an oxetane, is one of four structural features regarded to

122 While the source of the oxetane kinetic stability is yet to be characterized, it

123 sly with intramolecular OH transfer along an oxetane-like transition state.

124 ate in the stereospecific elaboration of the oxetane linkage was enone 22, which was susceptible to t

125 , followed by fragmentation of the resulting oxetanes, metal alkylidene-mediated strategies, [3 + 2]-

126 y associated with strong hydrogen bonding of oxetane moieties to the trehalose/sucrose matrix.

127 n acyl group to the tertiary hydroxyl on the oxetane moiety at C4 of the taxane ring demonstrates tha

128 The oxetane moiety of merrilactone A is fashioned via a Payn

129 NMR data for natural products containing the oxetane moiety, with the help of a recently developed pa

130 Notably, this methodology employs a keto-oxetane motif as a 1,4-dicarbonyl surrogate, which can b

131 erspective highlights recent applications of oxetane motifs in drug discovery campaigns, with emphasi

132 Oxetanocin A and albucidin are two oxetane natural products.

133 se matrix at room temperature, the bis-spiro-oxetane nitroxide radical possesses electron spin cohere

134 enzymes involved in the biosynthesis of the oxetane nucleosides albucidin and oxetanocin A.

135 Oxetanes offer exciting potential as structural motifs a

136 ampaigns, with emphasis on the effect of the oxetane on medicinally relevant properties and on the bu

137 an asymmetric hydrogen-bond-donor catalyzed oxetane opening with TMSBr that is shown to possess unex

138 tween organocatalysts in an enantioselective oxetane-opening reaction.

139 tility, the process was used to introduce an oxetane or azetidine into heteroaromatic systems that ha

140 a triscarbazole hole-transport group and an oxetane or benzocyclobutene crosslinkable group can be r

141 apparently these have never been applied to oxetanes or larger cyclic ethers.

142 ally available monomers, butylene oxide (BO)/oxetane (OX), tetrahydrofuran (THF), and phthalic anhydr

143 of nucleosides with novel base-constraining oxetane (OXE) modifications [oxetane, 1-(1',3'-O-anhydro

144 ive synthesis of highly functionalized spiro-oxetane oxindoles has been described.

145 iverse motifs of highly functionalized spiro-oxetane oxindoles of pharmaceutical relevance.

146 ) linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent

147 The alpha,alpha-difluoro-oxetane products are potential surrogates of oxetane, be

148 The oxetane products were further derivatized, while the rin

149 We compare the reactivity of oxetane radicals to other benzylic systems.

150 cycles through a facile Lewis-acid-catalyzed oxetane rearrangement.

151 thoxy group give rise to fused azetidines or oxetanes, respectively, via the same mechanism.

152 the effort involved recourse to a strategic oxetane ring (see compound 25).

153 ies of Taxol analogues demonstrates that the oxetane ring clearly operates by both mechanisms.

154 ts a previously unknown enzyme mechanism for oxetane ring formation.

155 The four-membered oxetane ring has been increasingly exploited for its con

156 The oxetane ring is an emergent, underexplored motif in drug

157 Here, we proposed that the oxetane ring is formed by cytochrome P450-mediated oxida

158 The enantioselective catalytic oxetane ring opening was employed as part of a three-ste

159 d-Hartwig conditions, followed by an in situ oxetane ring opening.

160 The facile formation of the strained oxetane ring provides strong support for the intermediac

161 critical steps, such as the formation of the oxetane ring, which is essential for its activity, have

162 ate ligand-protein steric effects around the oxetane ring.

163 ctively) to complete the biosynthesis of the oxetane ring.

164 the building blocks used to incorporate the oxetane ring.

165 tion events, leading to the formation of the oxetane ring.

166 d cyclic ether, followed by formation of the oxetane ring.

167 collision activation leads to the rupture of oxetane rings and the formation of diagnostic ions speci

168 e an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is

169 echanical damage of the network, four-member oxetane rings open to create two reactive ends.

170 Oxetanes show high product yields due to ring strain and

171 The network consists of an oxetane-substituted chitosan precursor incorporated into

172 first dyotropic rearrangement of an epoxide-oxetane substrate.

173 action was expanded to include the analogous oxetane substrates, revealing a hydroxymethyl handle in

174 ne, pyrrole, azetidine, tetrahydropyran, and oxetane substructures.

175 ay of sensitive functional groups, including oxetanes, sugar moieties, azetidines, tert-butyl carbama

176 Here, we report the development and use of oxetane sulfonyl fluorides (OSFs) and azetidine sulfonyl

177 Ex pathway under anionic conditions accesses oxetane-sulfur(VI) derivatives.

178 tions are successfully applied to synthesize oxetanes, tetrahydrofurans, and tetrahydropyrans but fai

179 tions, as are a number of literature acyclic oxetanes that could undergo similar retro-oxa-conjugate

180 The formation of oxetane, the reaction intermediate leading to (6-4) addu

181 With the oxiranes and oxetanes, the chloro derivative gave a different behavio

182 vated by substoichiometric concentrations of oxetane, THF, Et(2)O, and diisopropylamine are described

183 rix of four-membered rings-i.e., azetidines, oxetanes, thietanes, and cyclobutanes.

184 ative rates of attack of ammonia on oxirane, oxetane, thiirane, and thietane were determined computat

185 ew of the potential benefits of appending an oxetane to a drug compound, as well as potential pitfall

186 was also possible to convert epoxides and an oxetane to the dichlorinated products.

187 iven intramolecular rearrangement of 3-amido oxetanes to 2-oxazolines is the hallmark of this transfo

188 cile and unprecedented activation of 3-amido oxetanes to synthesize 2-oxazoline amide ethers using a

189 mitrephorone C, which is lacking the central oxetane unit but features a keto-function at C2, was not

190 Fragmentation of the oxetane via Lewis acid-activation results in the formati

191 ously to promote enantioselective opening of oxetanes via both Lewis and Bronsted acid mechanisms.

192 The oxetane was subjected to the mild reagent combination CB

193 ncluding alkylidene oxetanes and spirocyclic oxetanes, was highly stereoselective and directed by the

194 ocyclic oxetanes [2-oxo-spiro(3H-indole-3,2'-oxetanes)] were subjected to irradiation in the presence

195 similarly proposed to result in a transient oxetane, which fragments within a single elementary step

196 Oxetanes, which are normally unreactive, also participat

197 ntioselective intramolecular ring-opening of oxetanes with alcohols is catalyzed by (salen)Co(III) co

198 ioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration.

199 elective desymmetrization of 3,3-substituted oxetanes with higher enantiomeric excess in comparison t

200 ydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in exc