(S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one

Base Information

Chemical Name:(S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one
CAS No.:287717-36-6
Molecular Formula:C₃₈H₅₈INO₆S₂Si
Molecular Weight:844.004
Hs Code.:

(S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one

Synonyms:(S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one

There total 12 articles about (S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one 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:

: 1026273-04-0
(6E,8E,12E)-(2R,4S,5S,11S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-11-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-triene-1,3-dione

: 287717-36-6
(S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one

Guidance literature:: With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -25 - 0 ℃;
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

: 287717-36-6
(S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 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; various solvent(s) / 1 h / 0 °C / pH 7.0

6.1: 0.90 g / tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / -25 - 0 °C

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

Reference yield:

: 287717-35-5
(2E,4E,8E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-iodo-8-methyl-nona-2,4,8-trienal

: 287717-36-6
(S)-4-Benzyl-3-{(6E,8E,12E)-(2R,3R,4S,5S,11S)-11-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-13-iodo-4,12-dimethyl-2-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-trideca-6,8,12-trienoyl}-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: diethyl ether / -78 - -25 °C

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

2.1: 0.90 g / tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / -25 - 0 °C

With acetic acid; tetramethylammonium triacetoxyborohydride; In diethyl ether; acetonitrile;
DOI:10.1021/ja020091v