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

Base Information

Chemical Name:(2S,3R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidine-2-carboxylate
CAS No.:947373-41-3
Molecular Formula:C₂₉H₄₃NO₈SSi
Molecular Weight:593.814
Hs Code.:

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

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Chemical Property of (2S,3R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidine-2-carboxylate

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Technology Process of (2S,3R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidine-2-carboxylate

There total 4 articles about (2S,3R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-1-(toluene-4-sulfonyl)pyrrolidine-2-carboxylate 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: 78.0%

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

: 3970-21-6
2-Methoxyethoxymethyl chloride

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

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In chloroform; for 6h; Heating;
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

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

Guidance literature:: Multi-step reaction with 3 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

With boron trifluoride diethyl etherate; ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane; chloroform;
DOI:10.1021/jo070462w

Reference yield:

: 947373-38-8
(2R)-N-[2-(tert-butyldimethylsilyloxy)-3-oxopropyl]-4-methylbenzenesulfonamide

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

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / BF₃*OEt₂ / CH₂Cl₂ / 14 h / -78 °C

2: 78 percent / (i-Pr₂)NEt / CHCl₃ / 6 h / Heating

With boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In dichloromethane; chloroform;
DOI:10.1021/jo070462w