(E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione

Base Information

Chemical Name:(E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione
CAS No.:912651-30-0
Molecular Formula:C₄₀H₆₆O₇Si₂
Molecular Weight:715.131
Hs Code.:

(E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione

Synonyms:(E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione

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Chemical Property of (E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione

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Technology Process of (E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione

There total 9 articles about (E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione 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: 56.0%

: 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

: 912651-30-0
(E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione

Guidance literature:: With dmap; 4-(dimethylamino)pyridine hydrochloride; diisopropyl-carbodiimide; In chloroform; for 10h; Heating;
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

: 912651-30-0
(E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione

Guidance literature:: Multi-step reaction with 4 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

4.1: 56 percent / N,N'-diisopropylcarbodiimide; DMAP; DMAP*HCl / CHCl₃ / 10 h / Heating

With dmap; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; 4-(dimethylamino)pyridine hydrochloride; triethylamine; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform;
DOI:10.1021/ol0614020

Reference yield:

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

: 912651-30-0
(E)-(6S,10S,13R,14S,15S)-10,14-Bis-(tert-butyl-dimethyl-silanyloxy)-11,11,13,15-tetramethyl-6-((E)-(R)-1-methyl-3-phenyl-allyl)-1,7-dioxa-cyclohexadec-3-ene-2,8,12-trione

Guidance literature:: Multi-step reaction with 4 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

4.1: 56 percent / N,N'-diisopropylcarbodiimide; DMAP; DMAP*HCl / CHCl₃ / 10 h / Heating

With pyridine; dmap; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; 4-(dimethylamino)pyridine hydrochloride; triethylamine; diisopropyl-carbodiimide; In tetrahydrofuran; chloroform;
DOI:10.1021/ol0614020