(E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol

Base Information

Chemical Name:(E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol
CAS No.:850479-68-4
Molecular Formula:C₂₉H₅₂O₄Si
Molecular Weight:492.815
Hs Code.:

Synonyms:(E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol

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Chemical Property of (E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol

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Technology Process of (E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol

There total 4 articles about (E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol 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:

: 135708-75-7
{[(2R,3S)-1-(benzyloxy)-2-methylhex-5-en-3-yl]oxy}(tert-butyl)-dimethylsilane

: 850479-68-4
(E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / H₂ / Pd(OH)2/C / ethanol / 24 h

2.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - -20 °C

3.1: n-BuLi / toluene; hexane / -78 °C

3.2: ClTi(Oi-Pr)3; cC₅H₉MgCl / toluene; hexane; diethyl ether / -78 - -30 °C

3.3: BF₃*OEt₂ / toluene; hexane; diethyl ether / 1 h / -78 °C

With n-butyllithium; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In ethanol; hexane; dichloromethane; toluene; 2.1: Swern oxidation;
DOI:10.1021/ja050039+

Reference yield:

: 153762-87-9
(2S,3S)-2-methyl-3-(t-butyldimethylsilyloxy)hexanal

: 850479-60-6
(2R,3R,4R)-1-(benzyloxy)-2,4-dimethyl-5-heptyn-3-ol

: 850479-78-6
(E)-(2R,3R,4R,7S,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol

: 850479-68-4
(E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol

Guidance literature:: (2R,3R,4R)-1-(benzyloxy)-2,4-dimethyl-5-heptyn-3-ol; With n-butyllithium; In hexane; toluene; at -78 ℃;

With triisopropoxytitanium(IV) chloride; cyclopentylmagnesium chloride; In diethyl ether; hexane; toluene; at -78 - -30 ℃;

(2S,3S)-2-methyl-3-(t-butyldimethylsilyloxy)hexanal; With boron trifluoride diethyl etherate; In diethyl ether; hexane; toluene; at -78 ℃; for 1h;
DOI:10.1021/ja050039+

Reference yield:

: 850479-71-9
(2R,3S)-3-[(tert-butyldimethylsilyl)oxy]-2-methylhexan-1-ol

: 850479-68-4
(E)-(2R,3R,4R,7R,8R,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilanyloxy)-2,4,6,8-tetramethyldodec-5-ene-3,7-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - -20 °C

2.1: n-BuLi / toluene; hexane / -78 °C

2.2: ClTi(Oi-Pr)3; cC₅H₉MgCl / toluene; hexane; diethyl ether / -78 - -30 °C

2.3: BF₃*OEt₂ / toluene; hexane; diethyl ether / 1 h / -78 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; toluene; 1.1: Swern oxidation;
DOI:10.1021/ja050039+