83889-77-4

Basic information

• Product Name: (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid
• Synonyms: (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid
• CAS NO: 83889-77-4
• Molecular Weight: 368.389
• Mol File: 83889-77-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid(83889-77-4)
• EPA Substance Registry System: (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid(83889-77-4)

Safety Data

• Hazardous Substances Data: 83889-77-4(Hazardous Substances Data)

Upstream product

• 26339-42-4 (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 
• 56198-73-3 dimethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 67-56-1 methanol 

Downstream Products

• 28092-62-8 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione 
• 157378-76-2 C₁₉H₂₀N₂O₄ 
• 58-85-5 biotin 
• 31099-31-7 (3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile 
• 153991-84-5 (E)-5-[(3aR,6aS)-1,3-Dibenzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(6E)-ylidene]-pent-3-enoic acid 
• 367276-82-2 (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one 
• 154097-01-5 (3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-carbaldehyde 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 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

Chiral squaramide-mediated methanolytic desymmetrization of prochiral cyclic anhydride: A convenient approach for synthesizing roche lactone

The main objective of this report was to develop an improved process for the asymmetric synthesis of (3aS, 6aR)-lactone 1, which is the key chiral intermediate of (+)-biotin. This practical and efficient process includes a novel chiral squaramide alkamine derivatives 5 mediated methanolytic desymmetrization of prochiral cyclic anhydride 3 to produce the enantiomerically enriched precursor of Roche lactone.

A family of novel bifunctional organocatalysts: Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X7 receptor antagonists

A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield with up to 93% ee. The usefulness of this methodology was demonstrated in the asymmetric synthesis of the key intermediate of P2X7 receptor antagonists.

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.