(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol

Base Information

Chemical Name:(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol
CAS No.:1610887-99-4
Molecular Formula:C₂₆H₄₄O₄Si
Molecular Weight:448.718
Hs Code.:

Synonyms:(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol

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Chemical Property of (4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol

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Technology Process of (4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol

There total 9 articles about (4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol 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: 100.0%

: 1610887-98-3
ethyl-(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dienoate

: 1610887-99-4
(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol

Guidance literature:: ethyl-(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dienoate; With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.583333h; Inert atmosphere;

With rochelle salt; In hexane; dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1021/ol5011278

Reference yield: 63.0%

: 1610887-93-8
(S)-4-benzyl-3-{(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dienoyl}oxazolidin-2-one

: 1610887-99-4
(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol

Guidance literature:: With lithium borohydride; In methanol; diethyl ether; at 0 ℃; for 12h; Inert atmosphere;
DOI:10.1021/ol5011278

Reference yield:

: 1610887-87-0
(3R,4R)-3-(benzyloxy)-4-methoxyhex-5-ene-1-ol

: 1610887-99-4
(4S,5S,7R,8R,E)-7-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8-methoxy-2,4-dimethyldeca-2,9-dien-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.25 h / -78 - -45 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: titanium(IV) trichloride isopropoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 48 h / -50 °C / Inert atmosphere

2.3: 24 h / 20 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere

4.1: lithium borohydride / methanol; diethyl ether / 12 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; titanium(IV) trichloride isopropoxide; dimethyl sulfoxide; In methanol; diethyl ether; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1021/ol5011278