(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester
• CAS No.: 406684-07-9
• Molecular Formula: C₂₉H₄₁BrO₆Si
• Molecular Weight: 593.63
• Mol file: 406684-07-9.mol

Synonyms:(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester

Chemical Property of (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester

There total 2 articles about (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl 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: 79.0%

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester (406684-06-8) → (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester (406684-07-9)

Guidance literature:

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester; With sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; In water; acetonitrile; at 0 ℃; for 0.0833333h;

With sodium tetrahydroborate; In water; acetonitrile; at 0 ℃; for 0.5h;

With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester (406684-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HCl / methanol / 8 h / 0 - 20 °C

1.2: imidazole / CH₂Cl₂ / 0.17 h / 20 °C

1.3: 87 percent / N-methylmorpholine / CH₂Cl₂ / 2 h / 20 °C

2.1: (C₆H₅)I(OCOCF₃)2; NaHCO₃ / acetonitrile; H₂O / 0.08 h / 0 °C

2.2: NaBH₄ / acetonitrile; H₂O / 0.5 h / 0 °C

2.3: 79 percent / CBr₄; P(C₆H₅)3; N(C₂H₅)3 / CH₂Cl₂ / 2 h / 0 - 20 °C

With hydrogenchloride; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; In methanol; water; acetonitrile;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

Reference yield: 74.0%

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester (406684-07-9) → [(4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Guidance literature:

With N-ethylpiperidine hypophosphite; triethyl borane; In ethanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(02)01751-3

upstream raw materials:

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester

tert-butyldimethylsilyl chloride

Downstream raw materials:

[(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

(+)-ambruticin S

methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate

methyl 5β,6α-dibenzyloxypolyangioate