(8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl ester

Base Information

Chemical Name:(8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl ester
CAS No.:867372-42-7
Molecular Formula:C₂₇H₃₉NO₇
Molecular Weight:489.609
Hs Code.:

Synonyms:(8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl ester

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Chemical Property of (8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl ester

Chemical Property:

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Technology Process of (8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl ester

There total 7 articles about (8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl 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: 74.0%

: 867372-41-6
(S)-8-methoxy-9-oxonon-6-enoic acid tert-butyl ester

: 131685-53-5,101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: 867372-42-7
(8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl ester

Guidance literature:: (S)-4-benzyl-3-propionyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.5h;

(S)-8-methoxy-9-oxonon-6-enoic acid tert-butyl ester; In dichloromethane; at -78 - 20 ℃; for 18h;
DOI:10.1021/jo050942s

Reference yield:

: 867372-40-5
(S)-9-hydroxy-8-methoxynon-6-enoic acid tert-butyl ester

: 867372-42-7
(8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

2.1: dibutyl borontriflate; Hunig's base / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 74 percent / CH₂Cl₂ / 18 h / -78 - 20 °C

With di-n-butylboryl trifluoromethanesulfonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.1: Dess-Martin oxidation / 2.1: Evans asymmetric aldol reaction / 2.2: Evans asymmetric aldol reaction;
DOI:10.1021/jo050942s

Reference yield:

: 867372-50-7
6-(1-phenyl-1H-tetrazoly-5-ylsulfanyl)hexanoic acid tert-butyl ester

: 867372-42-7
(8S,9S,10S)-11-(4-benzyl-2-oxooxazolidin-3-yl)-9-hydroxy-8-methoxy-10-methyl-11-oxoundec-6-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / oxone / methanol / 20 h / 25 °C

2.1: KHMDS / 1,2-dimethoxy-ethane; toluene / 0.5 h

2.2: 76 percent / 1,2-dimethoxy-ethane; toluene / 3 h / -60 - 20 °C

3.1: 82 percent / TBAF / CH₂Cl₂; tetrahydrofuran / 3 h

4.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

5.1: dibutyl borontriflate; Hunig's base / CH₂Cl₂ / 0.5 h / 0 °C

5.2: 74 percent / CH₂Cl₂ / 18 h / -78 - 20 °C

With Oxone; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; toluene; 4.1: Dess-Martin oxidation / 5.1: Evans asymmetric aldol reaction / 5.2: Evans asymmetric aldol reaction;
DOI:10.1021/jo050942s