methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate

Base Information

Chemical Name:methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate
CAS No.:947373-46-8
Molecular Formula:C₂₅H₄₁NO₈SSi
Molecular Weight:543.754
Hs Code.:

Synonyms:methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate

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Chemical Property of methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate

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Technology Process of methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate

There total 6 articles about methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate 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:

: 947373-39-9
(2S,3R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-(toluene-4-sulfonyl)pyrrolidine-2-carboxylate

: 947373-46-8
methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / (i-Pr₂)NEt / CHCl₃ / 6 h / Heating

2: 88 percent / NaBH₄ / ethanol / 7 h / 20 °C

3: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 2.25 h / -60 - 0 °C

4: 315 mg / CH₂Cl₂ / 5 h / 0 - 20 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; chloroform; 3: Swern oxidation / 4: Wittig reaction;
DOI:10.1021/jo070462w

Reference yield:

: 947373-41-3
(2S,3R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidine-2-carboxylate

: 947373-46-8
methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / NaBH₄ / ethanol / 7 h / 20 °C

2: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 2.25 h / -60 - 0 °C

3: 315 mg / CH₂Cl₂ / 5 h / 0 - 20 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; 2: Swern oxidation / 3: Wittig reaction;
DOI:10.1021/jo070462w

Reference yield:

: 947373-42-4
(2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]methanol

: 947373-46-8
methyl (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]acrylate

Guidance literature:: Multi-step reaction with 2 steps

1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 2.25 h / -60 - 0 °C

2: 315 mg / CH₂Cl₂ / 5 h / 0 - 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Swern oxidation / 2: Wittig reaction;
DOI:10.1021/jo070462w