(3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-2-one

Base Information

Chemical Name:(3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-2-one
CAS No.:1250395-81-3
Molecular Formula:C₅₉H₁₀₄O₁₃Si₃
Molecular Weight:1105.72
Hs Code.:

(3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-2-one

Synonyms:(3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-2-one

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Chemical Property of (3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-2-one

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Technology Process of (3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-2-one

There total 1 articles about (3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-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: 54.0%

: 1250395-80-2
(2S,3R,5S,7R,8R,9S,11S,13R,15S,16Z,18R)-8-(tert-butyldimethylsilyloxy)-18-[(tertbutyldimethylsilyloxy)methyl]-5-(tert-butyldiphenylsilyloxy)-9,15-dihydroxy-3,7,13-trimethoxy-2,11-bis(methoxymethoxy)-10,10,16-trimethyl-16-icosenoic acid

: 1250395-81-3
(3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-2-one

Guidance literature:: (2S,3R,5S,7R,8R,9S,11S,13R,15S,16Z,18R)-8-(tert-butyldimethylsilyloxy)-18-[(tertbutyldimethylsilyloxy)methyl]-5-(tert-butyldiphenylsilyloxy)-9,15-dihydroxy-3,7,13-trimethoxy-2,11-bis(methoxymethoxy)-10,10,16-trimethyl-16-icosenoic acid; With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In toluene; at 0 - 20 ℃; for 24h;

With dmap; In toluene; at 20 ℃; for 24h; regioselective reaction;
DOI:10.1002/anie.201002293

Reference yield: 83.0%

: 1250395-81-3
(3S,4R,6S,8R,9R,10S,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-10-hydroxy-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecan-2-one

: 1250395-82-4
(3S,4R,6S,8R,9R,12S,14R,16S)-9-(tert-butyldimethylsilyloxy)-16-[(R,Z)-4-[(tertbutyldimethylsilyloxy)methyl]hex-2-en-2-yl]-6-(tert-butyldiphenylsilyloxy)-4,8,14-trimethoxy-3,12-bis(methoxymethoxy)-11,11-dimethyloxacyclohexadecane-2,10-dione

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 4h;
DOI:10.1002/anie.201002293