(S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester

Base Information

• Chemical Name: (S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester
• CAS No.: 172691-26-8
• Molecular Formula: C₃₃H₄₁BrO₅Si
• Molecular Weight: 625.675

Synonyms:(S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester

Chemical Property of (S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester

There total 1 articles about (S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester 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: 95.0%

(3S,4S,5R)-tert-butyl <6-(p-bromobenzyloxy)-4,5-epoxy-3-hydroxy>hexanoate (141277-18-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester (172691-26-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)01645-X

Reference yield: 98.0%

(S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester (172691-26-8) → (4S,5R)-5-[(S)-2-(4-Bromo-benzyloxy)-1-hydroxy-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one

Guidance literature:

With zinc(II) chloride; In dichloromethane; at 25 ℃; for 0.333333h;

DOI:10.1016/S0040-4039(00)91641-1

Reference yield:

(S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester (172691-26-8) → (4S,5S)-5-[(S)-2-(4-Bromo-benzyloxy)-1-hydroxy-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one (172691-22-4)

Guidance literature:

With chloro-trimethyl-silane; zinc; In dichloromethane; Yield given;

DOI:10.1016/0040-4039(95)01645-X

upstream raw materials:

(3S,4S,5R)-tert-butyl <6-(p-bromobenzyloxy)-4,5-epoxy-3-hydroxy>hexanoate

tert-butylchlorodiphenylsilane

Downstream raw materials:

(4S,5S)-5-[(S)-2-(4-Bromo-benzyloxy)-1-hydroxy-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one

(4S,5R,1'S)-5-<2'-<(4-Bromobenzyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane

Benzoic acid (R)-2-(4-bromo-benzyloxy)-1-[(2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-ethyl ester

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