(-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol

Base Information

Chemical Name:(-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol
CAS No.:133695-25-7
Molecular Formula:C₂₉H₃₆O₂Si
Molecular Weight:444.689
Hs Code.:

Synonyms:(-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol

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Chemical Property of (-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol

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Technology Process of (-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol

There total 8 articles about (-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-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:

: 133604-04-3
(2S)-5-bromo-1-O-((tert-butyldiphenyl)silyl)-2-methyl-3(E)-penten-1-ol

: 100-52-7
benzaldehyde

: 133604-05-4
(+)-(1R,2S,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol

: 133695-25-7
(-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol

Guidance literature:: With chromium chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 36h; Yield given. Yields of byproduct given;
DOI:10.1021/ja00011a025

Reference yield:

: 91751-24-5,92817-88-4,123284-89-9,112897-04-8
(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

: 133695-25-7
(-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

1.2: (+)-B-methoxydiisocampheylborane; boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C

1.3: ethanolamine / tetrahydrofuran; cyclohexane / 2.5 h / 0 °C

2.1: diethylaminosulfur trifluoride / CH₂Cl₂ / -45 - 20 °C

3.1: silica gel / CH₂Cl₂ / 20 °C

4.1: 30 mg / diethyl ether / 6 h / 20 °C

With diethylamino-sulfur trifluoride; sec.-butyllithium; silica gel; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane;
DOI:10.1021/ol060529m

Reference yield:

: 127665-68-3
(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

: 133695-25-7
(-)-(1S,2R,1'S)-2-[2'-(tert-butyldiphenylsilanyloxy)-1'-methylethyl]-1-phenylbut-3-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / PBr₃ / diethyl ether / 2 h / 22 °C

2: CrCl₃, LiAlH₄ / tetrahydrofuran / 36 h / 0 °C

With chromium chloride; lithium aluminium tetrahydride; phosphorus tribromide; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja00011a025