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

Base Information

• Chemical Name: (4S)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether
• CAS No.: 338385-66-3
• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.408
• Mol file: 338385-66-3.mol

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

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

There total 1 articles about (4S)-4-hydroxy-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: 35.0%

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) + phenylmagnesium bromide → (4S)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-66-3) + (4R)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-67-4)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

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

Reference yield: 88.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (4S)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-66-3) → (4S)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-68-5)

Guidance literature:

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

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

Reference yield:

(4S)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-66-3) → {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol (214678-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

2: 91 percent / H₂ / Pd/C / ethyl acetate / 6 h / 45 °C / 760 Torr

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

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

upstream raw materials:

4-O-benzyl-2,3-O-isopropylidene-D-threose

Downstream raw materials:

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

{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

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

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