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

Base Information

Chemical Name:(Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol
CAS No.:303727-89-1
Molecular Formula:C₂₃H₃₉BrO₄Si
Molecular Weight:487.55
Hs Code.:

Synonyms:(Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol

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Chemical Property of (Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol

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Technology Process of (Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol

There total 10 articles about (Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol 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: 85.0%

: 303727-88-0
(Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid ethyl ester

: 303727-89-1
(Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ja0015287

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 303727-89-1
(Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

2: 100 percent / DIBAL / tetrahydrofuran; hexane / 3.5 h / -78 °C

3: 75 percent / benzene / 40 h / Heating

4: 85 percent / DIBAL / CH₂Cl₂; hexane / -78 - 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; benzene; 1: silylation / 2: Reduction / 3: Condensation / 4: Reduction;
DOI:10.1021/ja0015287

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 303727-89-1
(Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: PPTS / CH₂Cl₂; cyclohexane / 43 h / 0 - 20 °C

2.1: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

3.1: DMSO; oxalyl chloride; iPr₂NEt / CH₂Cl₂ / -78 °C

4.1: n-Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - -8 °C

4.2: 63 percent / H₂O₂ / methanol / 10 h / 20 °C

5.1: AlMe₃ / tetrahydrofuran; hexane / 0 - 20 °C

5.2: 98 percent / tetrahydrofuran; hexane / 2.5 h / -20 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

7.1: 100 percent / DIBAL / tetrahydrofuran; hexane / 3.5 h / -78 °C

8.1: 75 percent / benzene / 40 h / Heating

9.1: 85 percent / DIBAL / CH₂Cl₂; hexane / -78 - 20 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; benzene; 1.1: Etherification / 2.1: Reduction / 3.1: Swern oxidation / 4.1: Evans aldol condensation / 4.2: Evans aldol condensation / 5.1: Metallation / 5.2: Substitution / 6.1: silylation / 7.1: Reduction / 8.1: Condensation / 9.1: Reduction;
DOI:10.1021/ja0015287