(3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate

Base Information

• Chemical Name: (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate
• CAS No.: 935872-19-8
• Molecular Formula: C₅₁H₉₁BrO₇Si₂
• Molecular Weight: 952.354
• Mol file: 935872-19-8.mol

Synonyms:(3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate

Chemical Property of (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate

There total 1 articles about (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate 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:

C51H91BrSi2O7C5H8O → (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate (935872-19-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 50 ℃; for 8h;

DOI:10.1021/jo062089i

Reference yield: 83.0%

(3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate (935872-19-8) → (3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1021/jo062089i

Reference yield:

(3S,4S,6S,8R,10S)-((S,3E,5Z)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate (935872-19-8) → (4S,5S,7S,9R,11S,13Z,15E,18S)-4-(tert-butyldimethylsilyloxy)-12-hydroxy-18-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-5,7,9,11-tetramethyl-13-[(triisopropylsilyloxy)methyl]oxacyclooctadeca-13,15-dien-2-one

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / 4 Angstroem molecular sieves; NMO; TPAP / CH₂Cl₂ / 0.75 h / 20 °C

2: 13 percent / CrCl₂; NiCl₂ / dimethylformamide / 12 h / 20 °C

With chromium dichloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; nickel dichloride; In dichloromethane; N,N-dimethyl-formamide; 2: Nozaki-Hiyama-Kishi reaction;

DOI:10.1021/jo062089i

Refernces