(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate

Base Information

Chemical Name:(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate
CAS No.:1421359-33-2
Molecular Formula:C₂₆H₄₂O₄Si
Molecular Weight:446.703
Hs Code.:

Synonyms:(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate

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Chemical Property of (2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate

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Technology Process of (2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate

There total 5 articles about (2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate 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: 99.0%

: 1421359-26-3
(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-ol

: 814-68-6,25189-84-8
acryloyl chloride

: 1421359-33-2
(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1021/jo302440a

Reference yield:

: 565454-94-6
(S)-(4-(benzyloxy)-3-methyl-2-methylenebutyl)trimethylsilane

: 1421359-33-2
(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: tin(IV) chloride / dichloromethane / 1 h / -78 °C

1.2: 0.83 h / -78 °C

2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

With tin(IV) chloride; triethylamine; In dichloromethane;
DOI:10.1021/jo302440a

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 1421359-33-2
(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl acrylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 48 h / 0 - 20 °C

2.1: cerium(III) chloride heptahydrate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 20 °C

3.1: amberlyst15 / hexane / 1 h / 20 °C

4.1: tin(IV) chloride / dichloromethane / 1 h / -78 °C

4.2: 0.83 h / -78 °C

5.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

With trifluorormethanesulfonic acid; cerium(III) chloride heptahydrate; tin(IV) chloride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; cyclohexane;
DOI:10.1021/jo302440a