(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-1-ol

Base Information

Chemical Name:(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-1-ol
CAS No.:214194-54-4
Molecular Formula:C₁₉H₃₀O₂Si
Molecular Weight:318.531
Hs Code.:

Synonyms:(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-1-ol

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Chemical Property of (4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-1-ol

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Technology Process of (4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-1-ol

There total 11 articles about (4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-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: 91.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 214194-53-3
tert-Butyl-dimethyl-[(S)-1-((R)-1-methyl-2-phenyl-ethyl)-prop-2-ynyloxy]-silane

: 214194-54-4
(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-1-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; for 4h; from -78 degC to rt.;
DOI:10.1016/S0040-4039(98)01421-X

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 214194-54-4
(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

2: K₂CO₃, H₂O / methanol / 3 h

3: 91 percent / n-BuLi / tetrahydrofuran / 4 h / from -78 degC to rt.

With 2,6-dimethylpyridine; n-butyllithium; water; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4039(98)01421-X

Reference yield:

: 14367-67-0
2-methyl-3-phenylpropionic acid

: 214194-54-4
(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hex-2-yn-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / EDC*HCl, Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

2: 5 percent / tetrahydrofuran / 0.5 h / from -78 to 0 degC

3: BH₃:SMe₂, chiral oxazaborolidine (S config.)

4: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 91 percent / n-BuLi / tetrahydrofuran / 4 h / from -78 degC to rt.

With 2,6-dimethylpyridine; dmap; n-butyllithium; dimethylsulfide borane complex; chiral oxazaborolidine (S config.); 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(98)01421-X