(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid

Base Information

Chemical Name:(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid
CAS No.:912651-29-7
Molecular Formula:C₄₀H₆₈O₈Si₂
Molecular Weight:733.146
Hs Code.:

(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid

Synonyms:(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid

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Chemical Property of (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid

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Technology Process of (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid

There total 8 articles about (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid 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: 82.0%

: 912651-28-6
(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-9-((2E,7E)-(5S,6R)-6-methyl-8-phenyl-5-triethylsilanyloxy-octa-2,7-dienoyloxy)-5-oxo-nonanoic acid 2-trimethylsilanyl-ethyl ester

: 912651-29-7
(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/ol0614020

Reference yield:

: 350493-51-5
(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid 2-trimethylsilanyl-ethyl ester

: 912651-29-7
(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 80 percent / H₂ / Pd/C / ethanol

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

2.2: 75 percent / DMAP / toluene / 4.5 h / 20 °C

3.1: 82 percent / TBAF / tetrahydrofuran / 2 h / 0 °C

With 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol;
DOI:10.1021/ol0614020

Reference yield:

: 869195-52-8
(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenylocta-2,7-dienoic acid

: 912651-29-7
(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((2E,7E)-(5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2,7-dienoyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 8.2 mg / pyridine / 0 - 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

2.2: 75 percent / DMAP / toluene / 4.5 h / 20 °C

3.1: 82 percent / TBAF / tetrahydrofuran / 2 h / 0 °C

With pyridine; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran;
DOI:10.1021/ol0614020