(12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one

Base Information

• Chemical Name: (12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one
• CAS No.: 488791-45-3
• Molecular Formula: C₅₆H₉₃NO₆SSi₃
• Molecular Weight: 992.68
• Mol file: 488791-45-3.mol

Synonyms:

Chemical Property of (12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one

There total 5 articles about (12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-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: 69.0%

(-)-(5S)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethylheptan-3-one (187527-25-9) + (6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal (488791-43-1) → (12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one (488791-45-3)

Guidance literature:

With lithium diisopropyl amide;

DOI:10.1039/b312213c

Reference yield:

5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,2-dimethyl-pentanoic acid phenyl ester (355009-03-9) → (12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one (488791-45-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / Et₃N

2: 69 percent / LDA

With triethylamine; lithium diisopropyl amide;

DOI:10.1039/b312213c

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one (488791-45-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / HB[-N(4-NO₂PhSO₂)-(R)-CH(i-Pr)COO-]

2: 77 percent / Et₃N

3: 69 percent / LDA

With HB[-N(4-NO₂PhSO₂)-(R)-CH(i-Pr)COO-]; triethylamine; lithium diisopropyl amide;

DOI:10.1039/b312213c

upstream raw materials:

(-)-(5S)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethylheptan-3-one

(6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal

3-(tert-butyldimethylsilanyloxy)propionaldehyde

5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,2-dimethyl-pentanoic acid phenyl ester

Downstream raw materials:

(12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one

(12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one