157378-76-2

Upstream product

• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 83889-77-4 (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid 
• 26339-42-4 (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 
• 1055329-68-4 (4S,5R)-1,3-dibenzyl-5-[(2E)-3-phenyl-2-propenyloxycarbonyl]-2-oxo-imidazolidine-4-carboxylic 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 academic research and scientific papers

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.

Novel asymmetric synthesis method for biotin chiral lactone

The invention discloses a novel asymmetric synthesis method for biotin chiral lactone. According to the method, by taking cycloanhydride as an initial raw material, the chiral lactone (3S,6R)-1,3-dibenzyl tetrahydrofuroimidazole-2,4-dione is prepared by selective alcoholysis, reduction and cyclization. The method is simple in process route, the raw material is cheap and easily available, and an alkaline catalyst is nearly insoluble in water and is recycled and reused through simple extraction, so that the production cost is lowered, and the diastereoselectivity of the alcoholysis reaction is improved. The method has the advantages of being simple to operate, mild in reaction condition, high in yield and high in stereoselectivity and has relatively good application value and economical benefits.

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.

Method for selectively dissociating cyclic carboxylic acid anhydrides

The invention relates to a method for selectively dissociating cyclic carboxylic acid anhydrides. According to the inventive method, a chiral amino alcohol with a tertiary amino group that may have a partially or completely bridged structure is used as the chiral auxiliary reagent.