(Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester

Base Information

• Chemical Name: (Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester
• CAS No.: 625109-72-0
• Molecular Formula: C₄₇H₆₄O₆Si₂
• Molecular Weight: 781.193
• Mol file: 625109-72-0.mol

Synonyms:(Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester

Chemical Property of (Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester

There total 1 articles about (Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl 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: 88.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate (475051-49-1) → (Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester (625109-72-0)

Guidance literature:

With trifluorormethanesulfonic acid; at 20 ℃;

DOI:10.1021/jo034901c

Reference yield: 74.0%

(Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester (625109-72-0) → (Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-en-1-ol (625109-73-1)

Guidance literature:

With diisobutylaluminium hydride; at -78 ℃; for 2h;

DOI:10.1021/jo034901c

Reference yield:

(Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester (625109-72-0) → (S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propionic acid ethyl ester

Guidance literature:

Multi-step reaction with 6 steps

1.1: 74 percent / DIBALH / 2 h / -78 °C

2.1: BH₃*THF / CH₂Cl₂; tetrahydrofuran / 1 h / 0 - 20 °C

2.2: 89 percent / CH₂Cl₂; tetrahydrofuran / -78 °C

3.1: 81 percent / DDQ; molecular sieves 4 Angstroem / 5 h / 0 °C

4.1: 73 percent / CSA

5.1: 89 percent / Bu₃SnH; Et₃B / toluene

With borane-THF; triethyl borane; 4 A molecular sieve; camphor-10-sulfonic acid; tri-n-butyl-tin hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; toluene; 2.1: Swern oxidation;

DOI:10.1021/jo034901c

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

Downstream raw materials:

(Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-en-1-ol

(Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enal

(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

(R)-2-Bromo-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propionic acid ethyl ester