4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester

Base Information

• Chemical Name: 4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester
• CAS No.: 185114-44-7
• Molecular Formula: C₂₉H₃₉BrO₆Si
• Molecular Weight: 591.615
• Mol file: 185114-44-7.mol

Synonyms:

Chemical Property of 4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester

There total 7 articles about 4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl 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: 94.0%

4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentylmethyl ester (185114-41-4) → 4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester (185114-44-7)

Guidance literature:

With pyridine-SO₃ complex; (Sia)2BH; dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0040-4039(97)10211-8

Reference yield:

(S)-3-Benzyloxymethoxy-4-oxo-butyric acid methyl ester → 4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester (185114-44-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent

2: 71 percent / CuI / -30 °C

3: 89 percent / Zn(BH₄)2

4: 92 percent / imidazole

5: DIBAL-H

6: pyridine

7: 94 percent / 1) (Sia)2BH, 2) DMSO, SO₃*pyridine, Et₃N

With pyridine; 1H-imidazole; copper(l) iodide; zinc(II) tetrahydroborate; pyridine-SO₃ complex; (Sia)2BH; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0040-4039(97)10211-8

Reference yield:

(1R,2R,3S,5S)-3-Benzyloxymethoxy-5-hydroxy-2-vinyl-cyclopentanecarboxylic acid methyl ester → 4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester (185114-44-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / imidazole

2: DIBAL-H

3: pyridine

4: 94 percent / 1) (Sia)2BH, 2) DMSO, SO₃*pyridine, Et₃N

With pyridine; 1H-imidazole; pyridine-SO₃ complex; (Sia)2BH; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0040-4039(97)10211-8

upstream raw materials:

4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentylmethyl ester

(E)-(S)-4-Benzyloxymethoxy-hex-2-enedioic acid dimethyl ester

(1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester

Downstream raw materials:

[(1S,2R,3R,4S)-4-Benzyloxymethoxy-2-iodomethyl-3-((Z)-oct-2-enyl)-cyclopentyloxy]-tert-butyl-dimethyl-silane

(Z)-(S)-7-[(1R,2R,3S,5S)-3-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-((Z)-oct-2-enyl)-cyclopentyl]-4-(tert-butyl-dimethyl-silanyloxy)-hept-5-enoic acid

1-[(Z)-(S)-7-[(1R,2R,3S,5S)-3-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-((Z)-oct-2-enyl)-cyclopentyl]-4-(tert-butyl-dimethyl-silanyloxy)-hept-5-enyloxymethyl]-4-methoxy-benzene