108732-21-4

Basic information

• Product Name: (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-(tert-butyldimethylsilyl)oxymethyl-5-pyrrolidone
• Synonyms: (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-(tert-butyldimethylsilyl)oxymethyl-5-pyrrolidone
• CAS NO: 108732-21-4
• Molecular Weight: 463.646
• Mol File: 108732-21-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-(tert-butyldimethylsilyl)oxymethyl-5-pyrrolidone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-(tert-butyldimethylsilyl)oxymethyl-5-pyrrolidone(108732-21-4)
• EPA Substance Registry System: (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-(tert-butyldimethylsilyl)oxymethyl-5-pyrrolidone(108732-21-4)

Safety Data

• Hazardous Substances Data: 108732-21-4(Hazardous Substances Data)

Upstream product

• 22129-07-3 N-benzyloxycarbonylimidazole 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 501-53-1 benzyl chloroformate 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 108732-20-3 (2S)-1-(tert-Butoxycarbonyl)-2-<(tert-butyldimethylsilyl)oxymethyl>pyrrolidine 

Downstream Products

• 108732-31-6 (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline methyl ester 
• 108732-28-1 (2S)-4-benzyloxycarbonyl-5-oxoproline tert-butyl ester 
• 71389-36-1 benzyl 4-(benzyloxycarbonyl)-2L,4DL-5-oxoprolinate 
• 108732-25-8 γ,γ,α-tribenzyl N-tert-butyloxycarbonyl-L-γ-carboxyglutamate 
• 108732-29-2 benzyl 1-(tert-butoxycarbonyl)-4-(benzyloxycarbonyl)-2L,4DL-5-oxoprolinate 
• 108732-27-0 N-(tert-butyloxycarbonyl)-γ,γ-dibenzyl-L-γ-carboxyglutamic acid α-tert-butyl ester 
• 108732-30-5 (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline tert-butyl ester 
• 53861-57-7 γ-carboxy-L-glutamic acid 
• 108732-23-6 (2S)-4-benzyloxycarbonyl-2-hydroxymethyl-5-pyrrolidone 
• 108732-22-5 (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-hydroxymethyl-5-pyrrolidone 

Relevant articles and documents

A New Approach for the Total Synthesis of L-γ-Carboxyglutamic Acid: Utility of Ruthenium Tetroxide Oxidation

A new and convenient synthesis of optically pure L-γ-carboxyglutamic acid (L-Gla)(1) from L-proline as a chiral source was developed.Protection of N-tert-butyloxycarbonyl(Boc)prolinol (4) with a tert-butyldimethylsilyl group followed by oxidation with ruthenium tetroxide (RuO4) afforded the corresponding lactam compound (6), which was carboxylated with lithium diisopropylamide and benzyloxycarbonylimidazole to afford the 4-benzyloxycarbonyl lactam derivative (7).Selective removal of the silyl group from 7, followed by oxidation of the resulting alcohol (8) with pyridinium dichromate gave the carboxylic acid, which was converted into the ester derivatives (10b-d).Cleavage of the lactam bond of 10b with excess benzyl alcohol in the presence of triethylamine gave γ,γ,α-tribenzyl N-Boc-L-γ-carboxyglutamate (11).Finally, 11 was hydrogenated over Pd on charcoal and deprotected with trifluoroacetic acid to produce L-γ-carboxyglutamic acid (1).Keywords - L-γ-carboxyglutamic acid; ruthenium tetroxide oxidation; carboxylation; L-proline; L-prolinol; 1-benzyloxycarbonylimidazole; 4-benzyloxycarbonyl-1-tert-butyloxycarbonyl-L-pyroglutamic acid ester; catalytic hydrogenation; trifluoroacetic acid deprotection