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

Base Information

Chemical Name:(2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]methanol
CAS No.:947373-42-4
Molecular Formula:C₂₂H₃₉NO₇SSi
Molecular Weight:489.706
Hs Code.:

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

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

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

There total 4 articles about (2R,3R,4R)-[4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidin-2-yl]methanol 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: 88.0%

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

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

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 20 ℃; for 7h;
DOI:10.1021/jo070462w

Reference yield:

: 947373-37-7
(2R,3E,5R)-1,6-di-(p-toluenesulfonylamido)-2,5-bis(tert-butyldimethylsilyloxy)-hex-3-ene

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C / 155.15 Torr

1.2: 81 percent / thiourea / CH₂Cl₂ / 3 h / 0 °C

2.1: 65 percent / BF₃*OEt₂ / CH₂Cl₂ / 14 h / -78 °C

3.1: 78 percent / (i-Pr₂)NEt / CHCl₃ / 6 h / Heating

4.1: 88 percent / NaBH₄ / ethanol / 7 h / 20 °C

With sodium tetrahydroborate; boron trifluoride diethyl etherate; ozone; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; chloroform;
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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine; In ethanol; chloroform;
DOI:10.1021/jo070462w