(R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate

Base Information

• Chemical Name: (R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate
• CAS No.: 1607830-33-0
• Molecular Formula: C₁₈H₂₈O₅Si
• Molecular Weight: 352.503
• Mol file: 1607830-33-0.mol

Synonyms:(R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate

Chemical Property of (R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate

There total 7 articles about (R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate 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: 79.0%

3-(tert-butyldimethylsilyloxy)glutaric anhydride (91424-40-7) + benzyl alcohol (100-51-6,185532-71-2) → (R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate (1607830-33-0)

Guidance literature:

With C₂₇H₃₁N₃O₃S; In tert-butyl methyl ether; enantioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201301374

Reference yield: 67.0%

3-(tert-butyldimethylsilyloxy)glutaric anhydride (91424-40-7) + benzyl alcohol (100-51-6,185532-71-2) → (S)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate + (R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate (1607830-33-0)

Guidance literature:

With xanthene-9-carboxylic acid; quinindine; In tert-butyl methyl ether; for 72h; Reagent/catalyst; Time; Temperature; enantioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201301374

Reference yield:

diethyl 3-hydroxyglutarate (32328-03-3) → (R)-monobenzyl 3-(tert-butyldimethylsilyloxy)glutarate (1607830-33-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-imidazole / dichloromethane

2: potassium hydroxide; water

3: acetic anhydride / 100 °C

4: C₂₇H₃₁N₃O₃S / tert-butyl methyl ether / 48 h

With 1H-imidazole; C₂₇H₃₁N₃O₃S; water; acetic anhydride; potassium hydroxide; In dichloromethane; tert-butyl methyl ether;

DOI:10.1002/ejoc.201301374

upstream raw materials:

3-(tert-butyldimethylsilyloxy)glutaric anhydride

benzyl alcohol

diethyl 3-hydroxyglutarate

tert-butyldimethylsilyl chloride

Refernces

• 1、 Ivsic, Trpimir,Dokli, Irena,Rimac, Ana,Hamersak, Zdenko. "Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups". . p. 631 - 638. Retrieved 2014/02/14.