(Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl ester

Base Information

• Chemical Name: (Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl ester
• CAS No.: 649755-87-3
• Molecular Formula: C₃₂H₅₆O₃SSi₂
• Molecular Weight: 577.032
• Mol file: 649755-87-3.mol

Synonyms:(Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl ester

Chemical Property of (Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl ester

There total 9 articles about (Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl 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:

(R)-4-benzyl-3-[(Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienoyl]-oxazolidin-2-one (649755-90-8) + phenylmethanethiol (100-53-8) → (Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl ester (649755-87-3)

Guidance literature:

With sodium hydroxide; n-butyllithium; In tetrahydrofuran; tert-butyl methyl ether; at 0 ℃; for 1.5h;

Reference yield:

(2R,3S,4R)-2,4-dimethyl-5-oxo-3-triethylsilanyloxypentanoic acid methoxymethylamide → (Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl ester (649755-87-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: chromium dichloride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

2.1: potassium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.67 h / -30 °C / Inert atmosphere

4.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.2: 0.75 h / -78 - 0 °C

5.1: 2,6-dimethylpyridine / dichloromethane / 3 h / -20 - 0 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

6.2: 1 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; chromium dichloride; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; potassium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; mineral oil;

DOI:10.1021/op049807s

Reference yield:

(Z)-(2R,3S,4S)-2,4-dimethyl-3-triethylsilanyloxyocta-5,7-dienoic acid methoxymethylamide → (Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienethioic acid S-benzyl ester (649755-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.67 h / -30 °C / Inert atmosphere

2.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.2: 0.75 h / -78 - 0 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 3 h / -20 - 0 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

4.2: 1 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/op049807s

upstream raw materials:

(R)-4-benzyl-3-[(Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienoyl]-oxazolidin-2-one

phenylmethanethiol

(Z)-(2R,3S,4S)-2,4-dimethyl-3-triethylsilanyloxyocta-5,7-dienal

(R)-4'-benzyl-3'-[(Z)-(2R,3S,4S,5S,6S)-3-hydroxy-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienoyl]-oxazolidin-2'-one