292151-19-0

Basic information

• Product Name: ethyl 5-((3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate
• Synonyms: ethyl 5-((3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate
• CAS NO: 292151-19-0
• Molecular Formula: C26H32N2O3S
• Molecular Weight: 452.618
• EINECS: -0
• Mol File: 292151-19-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: ethyl 5-((3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-((3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate(292151-19-0)
• EPA Substance Registry System: ethyl 5-((3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate(292151-19-0)

Safety Data

• Hazardous Substances Data: 292151-19-0(Hazardous Substances Data)

Upstream product

• 1236230-80-0 ethyl (3aS,4RS,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-4-hydroxy-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate 
• 1041862-06-9 ethyl 5-{(3aS,6aR)-1,3-dibenzyl-4-hydroxy-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl}-pentanoate 
• 109976-46-7 (5-ethoxy-5-oxopentyl)zinc(II) iodide 
• 541508-57-0 (2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetonitrile 
• 541508-55-8 (R)-3-benzyl-4-hydroxymethyl-2-oxothiazolidine 
• 541508-56-9 (R)-3-benzyl-2-oxothiazolidine-4-carbaldehyde 
• 98155-23-8 (R)-3-benzyl-2-oxothiazolidine-4-carboxylic acid 
• 112878-95-2 (4R,5R)-1,3-dibenzyl-5-(mercaptomethyl)imidazolidin-2-one-4-carboxylic acid 
• 541508-64-9 (4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxamide 
• 541508-59-2 (2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetamide 
• 541508-62-7 (4R,5R)-1,3-dibenzyl-3,3a,6,6a-tetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 41302-32-3 ethyl 5-iodopentanoate 
• 777940-99-5 2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetonitrile 

Downstream Products

• 58-85-5 biotin 
• 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

An improved asymmetric total synthesis of (+)-biotin via the enantioselective desymmetrization of a meso-cyclic anhydride mediated by cinchona alkaloid-based sulfonamide

The highly enantioselective total synthesis of (+)-biotin 1 via the Hoffmann-Roche lactone-thiolactone strategy has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid 2 with an overall yield of 35%. Two contiguous stereogenic centers at C-3a and C-6a were established through a rapid cinchona alkaloid-based sulfonamide-mediated enantioselective alcoholysis of meso-cyclic anhydride 3 to afford (4S,5R)-cinnamyl hemiester 4h, the direct precursor to (3aS,6aR)-lactone 5 with high enantioselectivity. A one-pot installation of the 4-carboxybutyl side chain was accomplished by a Fukuyama coupling reaction of (3aS,6aR)-thiolactone 6 with the organozinc reagent prepared from ethyl 5-bromopentanoate.

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.

Facile synthesis of (+)-biotin via Fukuyama coupling reaction

Treatment of a thiolactone 2 with a zinc reagent 3 in the presence of PdCl2(PPh3)2 (10 mol%) allowed installation of a C-2 side chain of (+)- biotin in a highly efficient manner, which enabled synthesis of (+)biotin in three steps from 2. (C) 2000 Elsevier Science Ltd.