(5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene

Base Information

Chemical Name:(5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene
CAS No.:1393661-54-5
Molecular Formula:C₃₉H₇₈O₅Si₄
Molecular Weight:739.387
Hs Code.:

Synonyms:(5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene

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Chemical Property of (5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene

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Technology Process of (5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene

There total 4 articles about (5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene 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: 92.0%

: 1393661-50-1
(2S,3S,6S,7S,E)-2-(benzyloxy)oct-4-ene-1,3,6,7-tetraol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1393661-54-5
(5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; for 3h; Reflux; Inert atmosphere;
DOI:10.1016/j.tet.2012.06.002

Reference yield:

: 1393661-52-3
(4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one

: 1393661-54-5
(5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene

Guidance literature:: Multi-step reaction with 3 steps

1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1.17 h / -78 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / methanol / 4 h / Reflux; Inert atmosphere

3: 1H-imidazole; dmap / dichloromethane / 3 h / Reflux; Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; pyridinium p-toluenesulfonate; In methanol; dichloromethane;
DOI:10.1016/j.tet.2012.06.002

Reference yield:

: 1393661-53-4
(3S,4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-ol

: 1393661-54-5
(5S,6S,9S,10S,E)-10-(benzyloxy)-6,9-bis(tert-butyldimethylsilyloxy)-2,2,3,3,5,13,13,14,14-nonamethyl-4,12-dioxa-3,13-disilapentadec-7-ene

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / methanol / 4 h / Reflux; Inert atmosphere

2: 1H-imidazole; dmap / dichloromethane / 3 h / Reflux; Inert atmosphere

With 1H-imidazole; dmap; pyridinium p-toluenesulfonate; In methanol; dichloromethane;
DOI:10.1016/j.tet.2012.06.002