(E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl ester

Base Information

• Chemical Name: (E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl ester
• CAS No.: 353797-09-8
• Molecular Formula: C₃₀H₅₃IO₆Si₂
• Molecular Weight: 692.823
• Mol file: 353797-09-8.mol

Synonyms:

Chemical Property of (E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl ester

There total 3 articles about (E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl 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:

(E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (210647-28-2) → (E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl ester (353797-09-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran

1.2: 83 percent / DMAP / benzene

2.1: HF*pyridine / pyridine; tetrahydrofuran

3.1: TfOH / diethyl ether

With trifluorormethanesulfonic acid; 2,4,6-trichlorobenzoyl chloride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; pyridine; diethyl ether; 1.1: Yamaguchi protocol;

DOI:10.1016/S0040-4039(02)00347-7

Reference yield:

(E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester (210647-32-8) → (E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl ester (353797-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1: HF*pyridine / pyridine; tetrahydrofuran

2: TfOH / diethyl ether

With trifluorormethanesulfonic acid; pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; diethyl ether;

DOI:10.1016/S0040-4039(02)00347-7

Reference yield:

N-(4-methoxybenzyl)-2,2,2-trichloroacetamide (123558-64-5) + (E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-hydroxy-1-methyl-propyl ester → (E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl ester (353797-09-8)

Guidance literature:

With trifluorormethanesulfonic acid; In diethyl ether;

DOI:10.1016/S0040-4039(02)00347-7

upstream raw materials:

N-(4-methoxybenzyl)-2,2,2-trichloroacetamide

(E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid

(E)-(3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hex-5-enoic acid (R)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester

Downstream raw materials:

[(4S,5S)-5-((E)-2-Iodo-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl ester