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

Base Information

• Chemical Name: (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether
• CAS No.: 338385-69-6
• Molecular Formula: C₂₆H₃₈O₄Si
• Molecular Weight: 442.671
• Mol file: 338385-69-6.mol

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

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

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-butyl benzyl ether

There total 2 articles about (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether 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: 85.4%

tert-butyldimethylsilyl chloride (18162-48-6) + (4R)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-67-4) → (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-69-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

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

Reference yield:

phenylmagnesium bromide → (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-69-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Grignard reaction;

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

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

upstream raw materials:

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

(+)-goniofufurone

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

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