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

Base Information

• Chemical Name: [(1S,2R,3R,4S)-4-Benzyloxymethoxy-2-iodomethyl-3-((Z)-oct-2-enyl)-cyclopentyloxy]-tert-butyl-dimethyl-silane
• CAS No.: 185114-47-0
• Molecular Formula: C₂₈H₄₇IO₃Si
• Molecular Weight: 586.669
• Mol file: 185114-47-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about [(1S,2R,3R,4S)-4-Benzyloxymethoxy-2-iodomethyl-3-((Z)-oct-2-enyl)-cyclopentyloxy]-tert-butyl-dimethyl-silane 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:

Methanesulfonic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-((Z)-oct-2-enyl)-cyclopentylmethyl ester → [(1S,2R,3R,4S)-4-Benzyloxymethoxy-2-iodomethyl-3-((Z)-oct-2-enyl)-cyclopentyloxy]-tert-butyl-dimethyl-silane (185114-47-0)

Guidance literature:

With sodium iodide; Yield given;

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

Reference yield:

(S)-3-Benzyloxymethoxy-4-oxo-butyric acid methyl ester → [(1S,2R,3R,4S)-4-Benzyloxymethoxy-2-iodomethyl-3-((Z)-oct-2-enyl)-cyclopentyloxy]-tert-butyl-dimethyl-silane (185114-47-0)

Guidance literature:

Multi-step reaction with 11 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

8: 93 percent / BuLi, HMPA

9: DIBAL-H

10: Et₃N

11: NaI

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; zinc(II) tetrahydroborate; pyridine-SO₃ complex; (Sia)2BH; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium iodide;

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

Reference yield:

(1R,2R,3S,5S)-3-Benzyloxymethoxy-5-hydroxy-2-vinyl-cyclopentanecarboxylic acid methyl ester → [(1S,2R,3R,4S)-4-Benzyloxymethoxy-2-iodomethyl-3-((Z)-oct-2-enyl)-cyclopentyloxy]-tert-butyl-dimethyl-silane (185114-47-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / imidazole

2: DIBAL-H

3: pyridine

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

5: 93 percent / BuLi, HMPA

6: DIBAL-H

7: Et₃N

8: NaI

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; pyridine-SO₃ complex; (Sia)2BH; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium iodide;

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

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

(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