(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid

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Chemical Name:(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid
CAS No.:877078-90-5
Molecular Formula:C₂₈H₄₃F₂NO₆Si
Molecular Weight:555.735
Hs Code.:

Synonyms:(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid

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Chemical Property of (2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid

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Technology Process of (2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid

There total 5 articles about (2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

: 877078-89-2
(2R,4R)-tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-(tert-butyldimethylsilyloxy)-3-oxopropyl)-4-(allyloxy)pyrrolidine-1-carboxylate

: 877078-90-5
(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid

Guidance literature:: (2R,4R)-tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-(tert-butyldimethylsilyloxy)-3-oxopropyl)-4-(allyloxy)pyrrolidine-1-carboxylate; With lithium hydroxide; water; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 2h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; pH=~ 2;

Reference yield:

: C₃₈H₅₂F₂N₂O₇Si

: 877078-90-5
(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid

Guidance literature:: With lithium hydroxide; water; dihydrogen peroxide; at 20 ℃; for 16h;

Reference yield:

: 877078-49-4
(S)-4-benzyl-3-(3-(3,5-difluorophenyl)propanoyl)oxazolidin-2-one

: 877078-90-5
(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-(tert-butyldimethylsilyloxy)propanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 - 20 °C

2: 2,6-dimethylpyridine / dichloromethane

3: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water

With 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.bmcl.2011.06.109