Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester

Base Information

Chemical Name:Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester
CAS No.:303727-90-4
Molecular Formula:C₂₄H₄₁BrO₆SSi
Molecular Weight:565.641
Hs Code.:

Synonyms:Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester

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Chemical Property of Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester

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Technology Process of Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester

There total 11 articles about Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl 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: 99.0%

: 124-63-0
methanesulfonyl chloride

: 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

: 303727-90-4
Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.0333333h;
DOI:10.1021/ja0015287

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 303727-90-4
Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 99 percent / Et₃N / CH₂Cl₂ / 0.03 h / 0 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; benzene; 1: silylation / 2: Reduction / 3: Condensation / 4: Reduction / 5: mesylation;
DOI:10.1021/ja0015287

Reference yield:

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

: 303727-90-4
Methanesulfonic acid (Z)-(4S,5R,6S)-2-bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 10 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

10.1: 99 percent / Et₃N / CH₂Cl₂ / 0.03 h / 0 °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 / 10.1: mesylation;
DOI:10.1021/ja0015287