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

Base Information

Chemical Name:(Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid ethyl ester
CAS No.:303727-88-0
Molecular Formula:C₂₅H₄₁BrO₅Si
Molecular Weight:529.587
Hs Code.:

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

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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-enoic acid ethyl ester

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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-enoic acid ethyl ester

There total 9 articles about (Z)-(4S,5R,6S)-2-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-2-enoic acid ethyl 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: 75.0%

: 212703-47-4
2,4-dideoxy-3-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-[(4-methoxyphenyl)-methyl]-2,4-dimethyl-L-arabinose

: 803-14-5
ethyl 2-bromo-2-(triphenylphosphoranylidene)acetate

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

: 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

Guidance literature:: In benzene; Heating;
DOI:10.1021/ja0015287

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 8 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

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;
DOI:10.1021/ja0015287