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Concise stereoselective synthesis of (2 S, 4 R)-4-hydroxyproline from (S)-O-benzylglycidol a novel cyclization

S Takano, Y Iwabuchi, K Ogasawara

文献索引：Takano, Seiichi; Iwabuchi, Yoshiharu; Ogasawara, Kunio Journal of the Chemical Society, Chemical Communications, 1988 ,  # 23  p. 1527 - 1528

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被引用次数: 17

摘要

Concise Stereoselective Synthesis of (2S,4R)-4-Hydroxyproline from (S)-0-Benzylglycidol by a Novel Cyclization ... Seiichi Takano," Yoshiharu Iwabuchi, and Kunio Ogasawara Pharmaceutical Institute, Tohoku University, Aoba yama, Sendai 980, Japan ... An efficient stereoselective route to (2S,4R)-4-hydroxyproIine from (S)-0-benzylglycidol has been established via a novel iodine-mediated cyclization of the N-benzoyl-y,G-unsaturated amide.

 相关合成线路
(2R)-1-benzyloxy-2-hydroxy-pent-4-yne结构式

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(2R)-1-benzylox...

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(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate结构式

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(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate结构式

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(2S,4R)-tert-bu...

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(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate结构式

121794-99-8

(2S,4R)-tert-bu...

(S)-1-(benzyloxy)pent-4-en-2-amine结构式

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(S)-1-(benzylox...

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(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate结构式

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(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide结构式

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(S)-N-(1-(benzy...

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(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate结构式

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(2S,4R)-tert-bu...

O-benzyl-(2S,4R)-4-benzoyloxyprolinol结构式

121794-97-6

O-benzyl-(2S,4R...

~%

(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate结构式

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(2S,4R)-tert-bu...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione结构式

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(S)-2-(1-(benzy...

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(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate结构式

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(2R)-1-benzyloxy-2-hydroxy-pent-4-yne结构式

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(2R)-1-benzylox...

~%

(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate结构式

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(S)-1-(benzyloxy)pent-4-en-2-amine结构式

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(S)-1-(benzylox...

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(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate结构式

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(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide结构式

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(S)-N-(1-(benzy...

~%

(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate结构式

121794-98-7

(2S,4R)-tert-bu...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione结构式

121794-94-3

(S)-2-(1-(benzy...

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(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate结构式

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(2S,4R)-tert-bu...

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide结构式

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(S)-N-(1-(benzy...

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O-benzyl-(2S,4R)-4-benzoyloxyprolinol结构式

121794-97-6

O-benzyl-(2S,4R...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne结构式

115352-39-1

(2R)-1-benzylox...

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O-benzyl-(2S,4R)-4-benzoyloxyprolinol结构式

121794-97-6

O-benzyl-(2S,4R...

(S)-1-(benzyloxy)pent-4-en-2-amine结构式

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(S)-1-(benzylox...

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O-benzyl-(2S,4R)-4-benzoyloxyprolinol结构式

121794-97-6

O-benzyl-(2S,4R...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione结构式

121794-94-3

(S)-2-(1-(benzy...

~%

O-benzyl-(2S,4R)-4-benzoyloxyprolinol结构式

121794-97-6

O-benzyl-(2S,4R...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne结构式

115352-39-1

(2R)-1-benzylox...

~%

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide结构式

121794-96-5

(S)-N-(1-(benzy...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione结构式

121794-94-3

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(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide结构式

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(S)-N-(1-(benzy...

苯甲酰氯结构式

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苯甲酰氯

(S)-1-(benzyloxy)pent-4-en-2-amine结构式

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(S)-1-(benzylox...

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(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide结构式

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(S)-N-(1-(benzy...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne结构式

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(2R)-1-benzylox...

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(S)-1-(benzyloxy)pent-4-en-2-amine结构式

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(S)-1-(benzylox...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione结构式

121794-94-3

(S)-2-(1-(benzy...

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(S)-1-(benzyloxy)pent-4-en-2-amine结构式

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(S)-1-(benzylox...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne结构式

115352-39-1

(2R)-1-benzylox...

~%

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione结构式

121794-94-3

(S)-2-(1-(benzy...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne结构式

115352-39-1

(2R)-1-benzylox...

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(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid结构式

121795-00-4

(2S,4R)-4-(benz...

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(2S,4R)-tert-bu...

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(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid结构式

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(2S,4R)-4-(benz...

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(S)-1-(benzylox...

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(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid结构式

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(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide结构式

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(S)-N-(1-(benzy...

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(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid结构式

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(2S,4R)-4-(benz...

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O-benzyl-(2S,4R...

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(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid结构式

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(2S,4R)-4-(benz...

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(2S,4R)-4-(benz...


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