(E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one

Base Information

Chemical Name:(E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one
CAS No.:647014-98-0
Molecular Formula:C₄₈H₈₈O₈Si₃
Molecular Weight:877.478
Hs Code.:

Synonyms:(E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one

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Chemical Property of (E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one

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Technology Process of (E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one

There total 8 articles about (E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-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: 68.0%

: 647014-94-6
(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-non-7-ynal

: 647014-97-9
[(3R,4S,5S,6R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-8-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-nonyl]-phosphonic acid dimethyl ester

: 647014-99-1
(E)-(2R,4R,5R,6S,7R,12S,13S)-4,13-Bis-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one

: 647014-98-0
(E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one

Guidance literature:: [(3R,4S,5S,6R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-8-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-nonyl]-phosphonic acid dimethyl ester; With barium dihydroxide; In tetrahydrofuran; at 25 ℃; for 0.5h;

(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-non-7-ynal; In tetrahydrofuran; water; at 0 - 25 ℃; for 0.5h;
DOI:10.1021/ja030496v

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 647014-98-0
(E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 25 °C

2.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 25 °C

2.2: tetrahydrofuran; H₂O / 0.5 h / 0 - 25 °C

With 2,6-dimethylpyridine; barium dihydroxide; In tetrahydrofuran; dichloromethane; 2.2: Horner-Wadsworth-Emmons coupling;
DOI:10.1021/ja030496v

Reference yield:

: 268736-76-1
tert-Butyl-[(S)-1-((S)-1-methoxy-but-3-enyl)-hex-4-ynyloxy]-dimethyl-silane

: 647014-98-0
(E)-(2R,4R,5S,6S,7R,12S,13S)-4,6,13-Tris-(tert-butyl-dimethyl-silanyloxy)-1,12-dimethoxy-2-(4-methoxy-benzyloxy)-5,7-dimethyl-octadec-9-en-16-yn-8-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 4-methylmorpholine N-oxide; osmium teroxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 5 h / 25 °C

2.1: 750 mg / aq. sodium periodate / 2-methyl-propan-2-ol; tetrahydrofuran / 3 h / 25 °C

3.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 25 °C

3.2: tetrahydrofuran; H₂O / 0.5 h / 0 - 25 °C

With barium dihydroxide; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol; 3.2: Horner-Wadsworth-Emmons coupling;
DOI:10.1021/ja030496v