26511-17-1

Basic information

• Product Name: 1,3,5-tribenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline
• Synonyms: 1,3,5-tribenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline
• CAS NO: 26511-17-1
• Molecular Weight: 425.487
• Mol File: 26511-17-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,3,5-tribenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-tribenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline(26511-17-1)
• EPA Substance Registry System: 1,3,5-tribenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline(26511-17-1)

Safety Data

• Hazardous Substances Data: 26511-17-1(Hazardous Substances Data)

Upstream product

• 26339-42-4 (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 
• 100-46-9 benzylamine 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 

Downstream Products

• 96666-55-6 4-(N-benzylcarbamoyl)-1,3-dibenzyl-2-oxoimidazole-5-carboxylate 
• 96666-51-2 1,3,5-tribenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline 
• 634188-85-5 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-ylidenepentane nitrile 
• 31099-31-7 (3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile 
• 863203-60-5 5-((3aS,6aR)-1,3-dibenzyl-4-hydroxy-2-oxohexyl-1H-furo[3,4-d]imidazol-4-yl)pentenoic acid 
• 452100-87-7 (3aS,4Z,6aR)-5-{hexahydro-1,3-dibenzyl-2-oxo-4H-thieno[3,4-d]imidazol-4-ylidene}pentanoic acid 
• 58-85-5 biotin 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 28092-62-8 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[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 
• 634188-84-4 (3aS,6R,6aR)-1,3,5-tribenzyl-6-hydroxytetrahydro-4H-pyrrolo[3,4-d]imidazole-2,4(1H)-dione 

Relevant articles and documents

Synthetic studies on d-biotin. Part 7: A practical asymmetric total synthesis of d-biotin via enantioselective reduction of meso-cyclic imide catalyzed by oxazborolidine

A novel and convenient method for the stereoselective synthesis of d-biotin 1 starting from the commercially available cis-1,3-dibenzyl-2- imidazolidone-4,5-dicarboxylic acid 2 has been developed. The key features of this synthesis include the enantioselective reduction of a meso-cyclic imide, mediated by a chiral oxazborolidine catalyst, derived from (1S,2S)-(+)-threo-1- (4-nitrophenyl)-2-amino-1,3-propanediol and the direct introduction of a C 5 side chain to the (3aS,6aR)-thiolactone through a modified di-Grignard reaction. Enantioselectivities of 98% in the oxazborolidine- catalyzed asymmetric reduction process have been achieved.

Synthetic Studies on d-Biotin, Part 6:1 An Expeditious and Enantiocontrolled Approach to the Total Synthesis of d-Biotin via a Polymer-Supported Chiral Oxazaborolidine-Catalyzed Reduction of meso-Cyclic Imide Strategy

An efficient and highly enantioselective synthesis of d-biotin from the known cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (5) was accomplished in 48% overall yield. The key reactions in the sequence involve the catalytic enantioselective reduction of meso-cyclic imide 6 using polymer-supported chiral oxazoborolidine, derived from (S)-α,α -diphenylprolinol and polymer-bound sulfonyl chloride, and the installation of the C5 side chain at C4 in the thiolactone 9 via a Ni/C-catalyzed Fukuyama coupling reaction.