(6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione

Base Information

Chemical Name:(6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione
CAS No.:287717-28-6
Molecular Formula:C₄₇H₅₇NO₆S₂Si
Molecular Weight:824.19
Hs Code.:

(6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione

Synonyms:(6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione

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Chemical Property of (6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione

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Technology Process of (6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione

There total 11 articles about (6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione 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:

: 287717-27-5
(2E,4E)-(S)-7-(tert-Butyl-diphenyl-silanyloxy)-nona-2,4-dien-8-ynal

: C₃₄H₅₀BNO₄S₂

: 287717-28-6
(6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione

Guidance literature:: In diethyl ether; at -78 - -20 ℃;
DOI:10.1016/S0040-4039(00)00504-9

Reference yield:

: 134916-00-0
(4S)-4-benzyl-3-(hex-5-enoyl)-1,3-oxazolidin-2-one

: 287717-28-6
(6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 77 percent / O₂; copper (I) chloride; palladium (II) chloride / dimethylformamide; H₂O

2.1: 98 percent / p-toluenesulfonic acid / acetic acid / 0.5 h

3.1: LDA / tetrahydrofuran / 1.5 h / -78 °C

3.2: 72 percent / tetrahydrofuran / 0.17 h / -78 °C

4.1: dimethylethylamine / diethyl ether / 2 h / 0 °C

5.1: diethyl ether / -78 - -25 °C

5.2: aq. hydrogen peroxide / methanol; CH₂Cl₂; various solvent(s) / 1 h / 0 °C / pH 7.0

With N,N-dimethyl-ethanamine; oxygen; toluene-4-sulfonic acid; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; water; acetic acid; N,N-dimethyl-formamide; 1.1: Wacker oxidation;
DOI:10.1021/ja020091v

Reference yield:

: 287717-24-2
(S)-4-Benzyl-3-[4-(2-methyl-[1,3]dithian-2-yl)-butyryl]-oxazolidin-2-one

: 287717-28-6
(6E,8E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8-dien-12-yne-1,3-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / 1.5 h / -78 °C

1.2: 72 percent / tetrahydrofuran / 0.17 h / -78 °C

2.1: dimethylethylamine / diethyl ether / 2 h / 0 °C

3.1: diethyl ether / -78 - -25 °C

3.2: aq. hydrogen peroxide / methanol; CH₂Cl₂; various solvent(s) / 1 h / 0 °C / pH 7.0

With N,N-dimethyl-ethanamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja020091v