(E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-enoic acid ethyl ester
CAS No.:155299-99-3
Molecular Formula:C₂₅H₄₂O₄Si
Molecular Weight:434.692
Hs Code.:

Synonyms:(E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-enoic acid ethyl ester

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Chemical Property of (E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-enoic acid ethyl ester

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Technology Process of (E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-enoic acid ethyl ester

There total 9 articles about (E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-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: 93.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 155299-98-2
(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

: 155299-99-3
(E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-enoic acid ethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile;
DOI:10.1016/S0040-4039(00)76541-5 DOI:10.1016/S0040-4039(00)76542-7

Reference yield: 93.0%

: 1067-74-9
Methyl diethylphosphonoacetate

: 155299-98-2
(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

: 155299-99-3
(E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-enoic acid ethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; for 20h;
DOI:10.1016/0040-4020(95)00201-I

Reference yield:

: 106357-30-6
1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

: 155299-99-3
(E)-(5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-oct-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

2: 1.) 9-BBN, 2.) H₂O₂, NaOH / 1.) THF, reflux, 2 h, 2.) THF, H₂O, r.t., 1 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

4: 93 percent / i-Pr₂NEt, LiCl / acetonitrile / 20 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In dichloromethane; acetonitrile;
DOI:10.1039/a804170i