(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

Base Information

Chemical Name:(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one
CAS No.:1375950-92-7
Molecular Formula:C₄₈H₈₄O₅Si₃
Molecular Weight:825.448
Hs Code.:

(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

Synonyms:(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

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Chemical Property of (3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

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Technology Process of (3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

There total 40 articles about (3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-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: 77.0%

: 1375950-73-4
(E)-(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

: 1375950-92-7
(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

Guidance literature:: (E)-(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate; With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 3.5h; Inert atmosphere;

With dimethyl sulfoxide; In dichloromethane; at 20 ℃; for 17h; Inert atmosphere;
DOI:10.1002/anie.201200871

Reference yield:

: 1174549-23-5
(Z)-5-((tert-butyldimethylsilyl)oxy)-3-iodopent-2-enoic acid

: 1375950-92-7
(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 2 h / 0 °C

1.2: 0.67 h / 0 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; benzene / 3.5 h / 50 - 55 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,4,6-trichlorobenzoyl chloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: Yamaguchi esterification / 1.2: Yamaguchi esterification / 2.1: Stille cross-coupling;
DOI:10.1002/anie.201108749

Reference yield:

: 1376331-05-3
(2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate

: 1375950-92-7
(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

3.1: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 3 h / -78 - -40 °C / Inert atmosphere

4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

5.1: Grubbs catalyst first generation / dichloromethane / 3.5 h / 20 °C / Inert atmosphere

5.2: 17 h / 20 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; 2,4,6-trichlorobenzoyl chloride; diisobutylaluminium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Yamaguchi esterification / 4.1: Stille coupling / 5.1: ring-closing metathesis (RCM);
DOI:10.1002/anie.201200871