(3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one

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Chemical Name:(3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one
CAS No.:1466415-13-3
Molecular Formula:C₅₀H₈₂O₈Si₂
Molecular Weight:867.367
Hs Code.:

(3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one

Synonyms:(3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one

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Chemical Property of (3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one

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Technology Process of (3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one

There total 8 articles about (3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-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: 60.0%

: 1466415-12-2
(2S,3R)-((3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyloxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-yl) 2-(benzyloxy)-3-methoxypent-4-enoate

: 1466415-13-3
(3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In 1,2-dichloro-ethane; at 80 ℃; for 11h;
DOI:10.1002/chem.201301796

Reference yield:

: 1466415-07-5
(3S,5S,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-methoxy-6,6-dimethyldec-9-enal

: 1466415-13-3
(3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C

1.2: 18 h / -78 °C

1.3: 1.5 h / 20 °C

2.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 0.08 h / -78 °C

2.2: 25 h / -78 - -20 °C

3.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 1 h

3.2: 1.5 h / 20 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 11 h / 80 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,4,6-trichlorobenzoyl chloride; tert.-butyl lithium; triethylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In diethyl ether; 1,2-dichloro-ethane; toluene; pentane;
DOI:10.1002/chem.201301796

Reference yield:

: 1466415-09-7
(3R,8S,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyloxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-one

: 1466415-13-3
(3S,4R,8R,10S,12R,14S,E)-3-(benzyloxy)-14-((R,Z)-4-(benzyloxymethyl)hex-2-en-2-yl)-8,10-bis(tert-butyldimethylsilyloxy)-4,12-dimethoxy-9,9-dimethyl-1-oxacyclo-tetradec-5-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 0.08 h / -78 °C

1.2: 25 h / -78 - -20 °C

2.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 1 h

2.2: 1.5 h / 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 11 h / 80 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,4,6-trichlorobenzoyl chloride; triethylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In 1,2-dichloro-ethane; toluene;
DOI:10.1002/chem.201301796