(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

Base Information

Chemical Name:(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
CAS No.:1466415-12-2
Molecular Formula:C₅₂H₈₆O₈Si₂
Molecular Weight:895.421
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 83.0%

: 1211323-42-0
(2S,3R)-2-(benzyloxy)-3-methoxypent-4-enoic acid

: 1466415-08-6
(3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol

: 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

Guidance literature:: (2S,3R)-2-(benzyloxy)-3-methoxypent-4-enoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; for 1h;

(3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol; With dmap; In toluene; at 20 ℃; for 1.5h;
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

: 1466415-12-2
(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

Guidance literature:: Multi-step reaction with 3 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

With 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; 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

: 1466415-12-2
(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

Guidance literature:: Multi-step reaction with 2 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

With 2,4,6-trichlorobenzoyl chloride; triethylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In toluene;
DOI:10.1002/chem.201301796