tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane

Base Information

Chemical Name:tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane
CAS No.:1392482-46-0
Molecular Formula:C₂₃H₃₆O₄Si
Molecular Weight:404.622
Hs Code.:

Synonyms:tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane

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Chemical Property of tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane

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Technology Process of tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane

There total 7 articles about tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane 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:

: 1392482-40-4
(3aR,4S,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde

: 1392482-35-7
diethyl 2-((tert-butyldimethylsilyloxy)methyl)benzylphosphonate

: 1392482-46-0
tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane

Guidance literature:: diethyl 2-((tert-butyldimethylsilyloxy)methyl)benzylphosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h; Inert atmosphere;

(3aR,4S,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde; In tetrahydrofuran; hexane; at 0 - 50 ℃; for 8h; Inert atmosphere;
DOI:10.1039/c2ob25069a

Reference yield:

: (2R,5S)-2-(benzyloxymethyl)-5-methyltetrahydrofuran-3,4-diol

: 1392482-46-0
tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 23 h / 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 20 °C / 750.08 Torr

3.1: Dess-Martin periodane / dichloromethane / 22 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / 0 °C / Inert atmosphere

4.2: 8 h / 0 - 50 °C / Inert atmosphere

With n-butyllithium; palladium 10% on activated carbon; hydrogen; pyridinium p-toluenesulfonate; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 4.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1039/c2ob25069a

Reference yield:

: 1043926-97-1
2-(tert-butyldimethylsilyloxymethyl)benzyl chloride

: 1392482-46-0
tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 5 h / 155 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / 0 °C / Inert atmosphere

2.2: 8 h / 0 - 50 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1039/c2ob25069a