(2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene

Base Information

Chemical Name:(2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene
CAS No.:460077-79-6
Molecular Formula:C₃₁H₄₈O₂Si₂
Molecular Weight:508.892
Hs Code.:

Synonyms:(2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene

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Chemical Property of (2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene

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Technology Process of (2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene

There total 5 articles about (2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene 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: 89.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 460077-78-5
(2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-3,6-nonadien-2-ol

: 460077-79-6
(2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1021/jo011102q

Reference yield:

: 21676-05-1
(3Z)-3-hexenyltriphenylphosphonium bromide

: 460077-79-6
(2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / 0 °C

1.2: 69 percent / tetrahydrofuran / 3 h / 0 °C

2.1: 90 percent / hydrochloric acid / H₂O; methanol / 4 h / 0 °C

3.1: 85 percent / triethylamine; 1,8-diazobicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 6 h / 20 °C

4.1: 89 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 20 °C

With hydrogenchloride; dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; 1.2: Wittig reaction;
DOI:10.1021/jo011102q

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 460077-79-6
(2S,3Z,6Z)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyldiphenylsilyl)oxy]-3,6-nonadiene

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / triethylamine; 1,8-diazobicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 6 h / 20 °C

2: 89 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 20 °C

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane;
DOI:10.1021/jo011102q