(E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester
• CAS No.: 468729-95-5
• Molecular Formula: C₂₄H₄₀O₅Si
• Molecular Weight: 436.664
• Mol file: 468729-95-5.mol

Synonyms:(E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester

Chemical Property of (E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester

There total 3 articles about (E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic 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: 65.0%

N-(4-methoxybenzyl)-2,2,2-trichloroacetamide (123558-64-5) + 7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid methyl ester (380229-23-2) → (E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester (468729-95-5)

Guidance literature:

With boron trifluoride diethyl etherate;

DOI:10.1016/S0040-4039(02)00993-0

Reference yield:

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal (104701-87-3) → (E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester (468729-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / tris(pentafluorophenyl)borane; isopropyl alcohol / diethyl ether / 6 h

2: 65 percent / BF₃*Et₂O

With boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate; isopropyl alcohol; In diethyl ether; 1: Mukaiyama aldol reaction;

DOI:10.1016/S0040-4039(02)00993-0

Reference yield:

tert-butyl(((1Z,3Z)-1-methoxypenta-1,3-dien-1-yl)oxy)dimethylsilane (172821-21-5) → (E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester (468729-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / tris(pentafluorophenyl)borane; isopropyl alcohol / diethyl ether / 6 h

2: 65 percent / BF₃*Et₂O

With boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate; isopropyl alcohol; In diethyl ether; 1: Mukaiyama aldol reaction;

DOI:10.1016/S0040-4039(02)00993-0

upstream raw materials:

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

7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid methyl ester

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

tert-butyl(((1Z,3Z)-1-methoxypenta-1,3-dien-1-yl)oxy)dimethylsilane

Downstream raw materials:

(2S,3S,4R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptane-1,3-diol

(S)-2-[(2S,4S,5R,6R)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propan-1-ol

{(2R,3R)-3-[(1S,2R,3S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-butyl]-oxiranyl}-methanol

(E)-(4R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol