(4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one

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Chemical Name:(4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one
CAS No.:1314768-41-6
Molecular Formula:C₃₆H₄₁NO₅Si
Molecular Weight:595.811
Hs Code.:

Synonyms:(4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one

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Chemical Property of (4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one

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Technology Process of (4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one

There total 5 articles about (4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one 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: 72.0%

: 1314768-39-2
(S,E)-1-benzyl-4-(benzyloxy)-5-(2-(tert-butyldiphenylsilyloxy)ethylidene)pyrrolidin-2-one

: 1314768-41-6
(4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one

Guidance literature:: With potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 3h; diastereoselective reaction;
DOI:10.1080/00397911.2010.503003

Reference yield:

: 1314768-35-8
(S)-1-benzyl-4-(benzyloxy)-5-ethynyl-5-hydroxy pyrrolidin-2-one

: 1314768-41-6
(4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 0.57 h / 0 °C / Inert atmosphere

3: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 3 h / 20 °C

With dmap; potassium osmate(VI) dihydrate; sodium tetrahydroborate; boron trifluoride diethyl etherate; 4-methylmorpholine N-oxide; triethylamine; In methanol; dichloromethane; water; acetone; 1: Meyer-Schuster rearrangement / 4: Sharpless asymmetric dihydroxylation;
DOI:10.1080/00397911.2010.503003

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1314768-41-6
(4S,5R)-1-benzyl-4-(benzyloxy)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-5-hydroxypyrrolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 3 h / 20 °C

With dmap; potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; water; acetone; 2: Sharpless asymmetric dihydroxylation;
DOI:10.1080/00397911.2010.503003