(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-hydroxyethyl)-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-hydroxyethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one
CAS No.:1375950-83-6
Molecular Formula:C₄₂H₇₀O₅Si₂
Molecular Weight:711.186
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-hydroxyethyl)-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-hydroxyethyl)-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-hydroxyethyl)-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-hydroxyethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

There total 39 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-hydroxyethyl)-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: 81.0%

: 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

: 1375950-83-6
(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-hydroxyethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃; for 4h; Inert atmosphere;
DOI:10.1002/anie.201200871

Reference yield:

: 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

: 1375950-83-6
(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-hydroxyethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

Guidance literature:: Multi-step reaction with 2 steps

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

2: pyridinium p-toluenesulfonate / methanol / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; pyridinium p-toluenesulfonate; In methanol; dichloromethane;
DOI:10.1002/anie.201108749

Reference yield:

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

: 1375950-83-6
(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-hydroxyethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

Guidance literature:: Multi-step reaction with 4 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

4.1: pyridinium p-toluenesulfonate / methanol / 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; pyridinium p-toluenesulfonate; triethylamine; In methanol; 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