541508-56-9

Basic information

• Product Name: 4-Thiazolidinecarboxaldehyde, 2-oxo-3-(phenylmethyl)-, (4R)-
• CAS NO: 541508-56-9
• Molecular Formula: C11H11NO2S
• Molecular Weight: 221.28
• Mol File: 541508-56-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-Thiazolidinecarboxaldehyde, 2-oxo-3-(phenylmethyl)-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolidinecarboxaldehyde, 2-oxo-3-(phenylmethyl)-, (4R)-(541508-56-9)
• EPA Substance Registry System: 4-Thiazolidinecarboxaldehyde, 2-oxo-3-(phenylmethyl)-, (4R)-(541508-56-9)

Safety Data

• Hazardous Substances Data: 541508-56-9(Hazardous Substances Data)

Upstream product

• 98155-23-8 (R)-3-benzyl-2-oxothiazolidine-4-carboxylic acid 
• 100-44-7 benzyl chloride 
• 541508-65-0 (4S)-4-ethylthiocarbonyl-3-benzylthiazolidin-2-one 
• 541508-55-8 (R)-3-benzyl-4-hydroxymethyl-2-oxothiazolidine 

Downstream Products

• 777940-99-5 2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetonitrile 
• 333355-49-0 5-[(3aR,6aS)-1,3-Dibenzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(6E)-ylidene]-pentanoic acid ethyl ester 
• 541508-64-9 (4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxamide 
• 541508-62-7 (4R,5R)-1,3-dibenzyl-3,3a,6,6a-tetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 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 
• 646030-83-3 (R)-3-Benzyl-4-(benzylamino-methyl)-thiazolidin-2-one 
• 541508-57-0 (2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetonitrile 
• 112878-95-2 (4R,5R)-1,3-dibenzyl-5-(mercaptomethyl)imidazolidin-2-one-4-carboxylic acid 
• 541508-59-2 (2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetamide 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 

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.

INTERMEDIATE FOR BIOTIN AND PROCESS FOR PRODUCING THE SAME

The present invention is to provide a process for preparing a synthetic intermediate of biotin which is industrially advantageous, and discloses a process for preparing a compound represented by the formula (I) : ???wherein R1 and R2 may be the same or different from each other, and each represents hydrogen atom, a benzyl group which may have a substituent(s) on the benzene ring, a benzhydryl group which may have a substituent(s) on the benzen ring, or a trityl group which may have a substituent(s) on the benzene ring, R3 represents cyano group, carboxyl group, an alkoxycarbonyl group, an alkylthiocarbonyl group, or a carbamoyl group which may have a substituent, or a salt thereof which comprises subjecting a compound represented by the formula (II-a) : ???wherein the symbols have the same meanings as defined above, or a salt thereof to ring transformation.

2-Thiazolidinone: A novel thiol protective surrogate of complete atom efficiency, a practical synthesis of (+)-biotin

2-Thiazolidinone derivatives were shown to be novel protective surrogates of a thiol group in L-cysteine derivatives. After elaboration at the C-4 substituent, the thiol group was completely liberated by simple heating in DMF whose atom efficiency is 100%. A practical synthesis of (+)-biotin was accomplished by the use of the strategy employing 4-functionalized 2-thiazolidinone derivatives as the intermediates, allowing a synthesis of (+)-biotin in 10 steps and in 31% overall yield. Short steps, high yield, and ease of operation of the present approach would permit the hitherto most efficient access to (+)-biotin.