(4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol

Base Information

• Chemical Name: (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol
• CAS No.: 214678-58-7
• Molecular Formula: C₁₉H₃₂O₄Si
• Molecular Weight: 352.546
• Mol file: 214678-58-7.mol

Synonyms:(4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol

Chemical Property of (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol

There total 5 articles about (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol 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: 100.0%

(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester → (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol (214678-58-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(98)01562-7

Reference yield: 97.0%

(4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-69-6) → (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol (214678-58-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 45 ℃; for 6h; under 760 Torr;

DOI:10.1016/S0040-4020(01)00050-3

Reference yield:

phenylmagnesium bromide → (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol (214678-58-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / tetrahydrofuran / -78 - 20 °C

2: 85.4 percent / imidazole / dimethylformamide / 24 h / 20 °C

3: 97 percent / H₂ / Pd/C / ethyl acetate / 6 h / 45 °C / 760 Torr

With 1H-imidazole; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 1: Grignard reaction;

DOI:10.1016/S0040-4020(01)00050-3

upstream raw materials:

(4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether

tert-butyldimethylsilyl chloride

(4R)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether

Downstream raw materials:

Trifluoro-methanesulfonic acid (4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

(+)-goniofufurone

ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate