157378-76-2

Basic information

• Product Name: C₁₉H₂₀N₂O₄
• Synonyms: C₁₉H₂₀N₂O₄
• CAS NO: 157378-76-2
• Molecular Weight: 340.379
• Mol File: 157378-76-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: C₁₉H₂₀N₂O₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₉H₂₀N₂O₄(157378-76-2)
• EPA Substance Registry System: C₁₉H₂₀N₂O₄(157378-76-2)

Safety Data

• Hazardous Substances Data: 157378-76-2(Hazardous Substances Data)

Upstream product

• 1055329-68-4 (4S,5R)-1,3-dibenzyl-5-[(2E)-3-phenyl-2-propenyloxycarbonyl]-2-oxo-imidazolidine-4-carboxylic acid 
• 26339-42-4 (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 
• 83889-77-4 (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 332908-83-5 C₃₈H₃₈N₄O₅ 
• 332908-81-3 C₃₆H₄₅N₃O₅ 
• 86384-60-3 C₃₀H₃₃N₃O₅ 
• 86420-32-8 C₃₀H₃₃N₃O₅ 
• 332908-75-5 C₃₀H₃₃N₃O₅ 

Downstream Products

• 28092-62-8 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione 
• 87585-00-0 (4S,5R)-1,3-dibenzyl-5-hydroxymethyl-2-oxoimidazolidine-4-carboxylic acid lactone 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 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 

Relevant articles and documents

Synthetic studies on (+)-biotin, part 151: A chiral squaramide-mediated enantioselective alcoholysis approach toward the total synthesis of (+)-biotin

An efficient stereocontrolled total synthesis of (+)-biotin (1) has been achieved via the intermediacy of Roche's lactone 5 starting from cis-1,3-dibenzyl-2-imidazole-4,5-dicarboxylic acid (2). The bifunctional cinchona alkaloid-derived squaramide-promoted enantioselective alcoholysis was utilizing as a tool for the construction of two contiguous stereocenters of C-3a and C-6a in biotin molecular with excellent enantioselectivity. In addition, the 4-carboxybutyl side chain was assembled by first using C4+C1 approach via a novel tricyclic thiophanium salt intermediate.

Synthetic studies on (+)-biotin, Part 11:[1] Application of Cinchona alkaloid-mediated asymmetric alcoholysis of meso-cyclic anhydride in the total synthesis of (+)-biotin

A practical and asymmetric process for the totalsyn thesis of (+)-biotin (1) has been accomplished starting from cis-1,3-dibenzyl-2-oxoimidazolidine-4,5- dicarboxylic acid (2). This approach features a highly enantioselective alcoholysis of mesocyclic anhydride 3 into (4S,5R)-cinnamylhemiest er 4 mediated by Cinchona alkaloids. Another attractive feature of this synthesis involves the use of recyclable palladium nanoparticles-catalyzed assembly of the 4-carboxybutyl chain at C-4 in (3aS,6aR)-thiolactone 7 employing an improved Fukuyamatype cross-coupling reaction.