112878-95-2

Basic information

• Product Name: 4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)-
• CAS NO: 112878-95-2
• Molecular Formula: C19H20N2O3S
• Molecular Weight: 356.445
• Mol File: 112878-95-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)-(112878-95-2)
• EPA Substance Registry System: 4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)-(112878-95-2)

Safety Data

• Hazardous Substances Data: 112878-95-2(Hazardous Substances Data)

Upstream product

• 98155-23-8 (R)-3-benzyl-2-oxothiazolidine-4-carboxylic acid 
• 541508-57-0 (2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetonitrile 
• 646512-43-8 (1R,2S,4R)-3-benzyl-4-carbamoyl-2-oxo-2-phenylimidazo[1,5-c]thiazolidine 
• 541508-55-8 (R)-3-benzyl-4-hydroxymethyl-2-oxothiazolidine 
• 541508-56-9 (R)-3-benzyl-2-oxothiazolidine-4-carbaldehyde 
• 777940-99-5 2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetonitrile 
• 541508-59-2 (2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetamide 
• 541508-64-9 (4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxamide 
• 541508-63-8 (4S,4'S,5R,5'R)-5,5'-[dithiobis-(methylene)]bis(1,3-dibenzyl-2-oxoimidazolidin-4-carboxamide) 

Downstream Products

• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 541508-62-7 (4R,5R)-1,3-dibenzyl-3,3a,6,6a-tetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 58-85-5 biotin 
• 333355-49-0 5-[(3aR,6aS)-1,3-Dibenzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(6E)-ylidene]-pentanoic acid ethyl ester 
• 292151-18-9 ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate 
• 292151-19-0 (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester 
• 33607-60-2 (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid 

Relevant articles and documents

A practical synthesis of (+)-biotin from L-cysteine

α-Amino aldehyde 4, which is readily derived from L-cysteine through cyclization and elaboration of the carboxy group, was subjected to the Strecker reaction, which, via sodium bisulfite adduct 16, afforded α-amino nitrile 5 with high diastereose-lectivity (syn/anti = 11:1) and in high yield. Amide 6, derived from 5, was converted to thiolactone 8, a key intermediate in the synthesis of (+)-biotin (1), by a novel S,N-carbonyl migration and cyclization reaction. The Fukuyama coupling reaction of 8 with the zinc reagent 21, which has an ester group, in the presence of a heterogeneous Pd/ C catalyst allowed the efficient installation of the 4-carboxybutyl chain to provide 9. Compound 9 was hydrogenated and the protecting groups removed to furnish 1 in 10 steps and in 34 % overall yield from L-cysteine.

An efficient and practical procedure for Strecker reaction: A highly diastereoselective synthesis of a key intermediate for (+)-biotin

Treatment of α-amino aldehyde 2, which was prepared through Moffatt oxidation of the corresponding β-amino alcohol 5, with aqueous sodium bisulfite allowed clean conversion to a water-soluble bisulfite adduct 6 [>99% conversion, 89% yield (two steps)]. The aqueous solution of 6 was treated with benzylamine followed by easy-handling NaCN to effect the Strecker reaction to afford α-amino nitrile 3 with high diastereoselectivity and in high yield (syn/anti = 11:1, 95% assay yield). Both the compounds syn-3 and anti-3 were converted to a key intermediate 4 for (+)-biotin through S,N-carbonyl migration in high yields.

A Facile Synthesis of a Key Intermediate for (+)-Biotin via Strecker Reaction

The Strecker reaction of (2R,4R)-2-phenyl-3-phenoxycarbonylthiazolidine-4- carbaldehyde (4b), which was readily prepared from L-cysteine, with benzylamine and trimethylsilyl cyanide provided α-amino nitrile 5b stereoselectively (syn-anti, 2:1), Amidation of 5b and subsequent cyclization gave bicyclic compound 6, which, upon reduction with zinc dust, hydrolysis and subsequent cyclization, furnished thiolactone 2, a key intermediate for (+)-biotin (1).