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

Base Information

Chemical Name:methyl (2R,3R,4R)-3-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]propionate
CAS No.:947373-47-9
Molecular Formula:C₂₅H₄₃NO₈SSi
Molecular Weight:545.77
Hs Code.:

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

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

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

There total 7 articles about methyl (2R,3R,4R)-3-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]propionate 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%

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

: 947373-47-9
methyl (2R,3R,4R)-3-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]propionate

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 6h;
DOI:10.1021/jo070462w

Reference yield:

: C₂₂H₃₇NO₇SiS

: 947373-47-9
methyl (2R,3R,4R)-3-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]propionate

Guidance literature:: Multi-step reaction with 2 steps

1: 315 mg / CH₂Cl₂ / 5 h / 0 - 20 °C

2: 93 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C

With hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate; 1: Wittig reaction;
DOI:10.1021/jo070462w

Reference yield:

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

: 947373-47-9
methyl (2R,3R,4R)-3-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]propionate

Guidance literature:: Multi-step reaction with 5 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

5: 93 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C

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