(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

Base Information

• Chemical Name: (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
• CAS No.: 1026273-04-0
• Molecular Formula: C₃₈H₅₆INO₆S₂Si
• Molecular Weight: 841.988

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 10 articles about (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 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:

(2E,4E,8E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-iodo-8-methyl-nona-2,4,8-trienal (287717-35-5) + C34H50BNO4S2 → (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 (1026273-04-0)

Guidance literature:

In diethyl ether; at -78 - -20 ℃;

DOI:10.1016/S0040-4039(00)00504-9

Reference yield:

(4S)-4-benzyl-3-(hex-5-enoyl)-1,3-oxazolidin-2-one (134916-00-0) → (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 (1026273-04-0)

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; 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:

(S)-4-Benzyl-3-[4-(2-methyl-[1,3]dithian-2-yl)-butyryl]-oxazolidin-2-one (287717-24-2) → (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 (1026273-04-0)

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; 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

upstream raw materials:

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

(4S)-4-benzyl-3-(hex-5-enoyl)-1,3-oxazolidin-2-one

1-(4(S)-Benzyl-2-oxo-oxazolidin-3-yl)-hexane-1,5-dione

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

Downstream raw materials:

C₆₀H₈₉N₅O₁₂

C₄₃H₅₉IN₄O₁₀

3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionic acid 2-trimethylsilanyl-ethyl ester

C₃₈H₅₁IN₄O₈

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