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

Base Information

Chemical Name:(2R,3R,4R)-methyl 4-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]butyrate
CAS No.:947373-44-6
Molecular Formula:C₂₆H₄₅NO₈SSi
Molecular Weight:559.797
Hs Code.:

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

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

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

There total 6 articles about (2R,3R,4R)-methyl 4-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]butyrate 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: 57.0%

: 947373-43-5
(2S,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-iodomethyl-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidine

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 947373-44-6
(2R,3R,4R)-methyl 4-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]butyrate

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 4.5h; Heating;
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

: 947373-44-6
(2R,3R,4R)-methyl 4-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]butyrate

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: 86 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 12 h / Heating

4: 57 percent / Bu₃SnH; AIBN / benzene / 4.5 h / Heating

With 1H-imidazole; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In ethanol; dichloromethane; chloroform; benzene;
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

: 947373-44-6
(2R,3R,4R)-methyl 4-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]butyrate

Guidance literature:: Multi-step reaction with 3 steps

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

2: 86 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 12 h / Heating

3: 57 percent / Bu₃SnH; AIBN / benzene / 4.5 h / Heating

With 1H-imidazole; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; triphenylphosphine; In ethanol; dichloromethane; benzene;
DOI:10.1021/jo070462w