51591-75-4

Usage

Uses

Used in Pharmaceutical Industry:
CIS-1,3-DIBENZYL-2-OXO-4,5-IMIDAZOLIDINEDICARBOXYLIC ACID is used as a reagent in the total synthesis of Biotin for its vital role in various biological processes. Biotin is essential for the production of certain fatty acids, the synthesis of certain amino acids, and the production of hormones and cholesterol. It also plays a crucial role in the metabolism of carbohydrates and the conversion of fats to energy.
Used in Nutritional Supplements:
CIS-1,3-DIBENZYL-2-OXO-4,5-IMIDAZOLIDINEDICARBOXYLIC ACID contributes to the production of Biotin, which is used as a nutritional supplement to support healthy skin, hair, and nails. Biotin deficiency can lead to hair loss, and its supplementation is believed to help maintain healthy hair and nails.
Used in Research and Development:
CIS-1,3-DIBENZYL-2-OXO-4,5-IMIDAZOLIDINEDICARBOXYLIC ACID is used as a reagent in the research and development of new drugs and therapies that target Biotin-dependent enzymes and pathways. This can lead to the discovery of novel treatments for various diseases and conditions, including cancer, where the biotin content is higher in tumor tissues compared to normal tissue.
Used in Diagnostic Applications:
CIS-1,3-DIBENZYL-2-OXO-4,5-IMIDAZOLIDINEDICARBOXYLIC ACID can be employed in the development of diagnostic tools and tests that measure Biotin levels in biological samples. This can help in the early detection of Biotin deficiency and monitor the effectiveness of Biotin supplementation in patients.

InChI:InChI=1/C19H18N2O5/c22-17(23)15-16(18(24)25)21(12-14-9-5-2-6-10-14)19(26)20(15)11-13-7-3-1-4-8-13/h1-10,15-16H,11-12H2,(H,22,23)(H,24,25)/t15-,16+

Upstream product

• 75-44-5 phosgene 
• 55645-40-4 (2R,3S)-2,3-bis(benzylamino)succinic acid 
• 21035-81-4 (3aRS,6SR,6aSR)-1,3-dibenzyl-6-hydroxy-3,3a,6,6a-tetrahydro-1H-furo<3,4-d>imidazole-2,4-dione 
• 14464-17-6 N,N-dibenzyl-aspartic acid 
• 87585-00-0 (4S,5R)-1,3-dibenzyl-5-hydroxymethyl-2-oxoimidazolidine-4-carboxylic acid lactone 
• 26339-42-4 (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 
• 28092-55-9 Acetic acid (3aR,4R,6aS)-1,3-dibenzyl-2,6-dioxo-hexahydro-furo[3,4-d]imidazol-4-yl ester 
• 129388-92-7 (3aR,6S,6aS)-1,3-dibenzyl-6-hydroxy-3,3a,6,6a-tetrahydro-1H-furo<3,4-d>imidazole-2,4-dione 

Downstream Products

• 56198-73-3 dimethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate 
• 83889-74-1 (4S,5R)-1,3-Dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid dipropyl ester 
• 26339-42-4 (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 
• 56198-32-4 cis-1,3-dibenzyl-4,5-dihydroxymethyl-imidazolidin-2-one 
• 26511-17-1 1,3,5-tribenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline 
• 154097-01-5 (3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-carbaldehyde 
• 83889-77-4 (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic 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 
• 153991-84-5 (E)-5-[(3aR,6aS)-1,3-Dibenzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(6E)-ylidene]-pent-3-enoic acid 
• 56198-34-6 (3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 350228-40-9 1,3-dibenzyl-4,5-cis-bis(chloromethyl)-2-imidazolidone 
• 87585-00-0 (4S,5R)-1,3-dibenzyl-5-hydroxymethyl-2-oxoimidazolidine-4-carboxylic acid lactone 
• 83889-76-3 (4S,5R)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid 
• 40222-71-7 cis-1,3-dibenzyl-hexahydro-1H-furo[3,4-d]imidazole-2,4-dione 

Relevant academic research and scientific papers

Conversion method of 1, 3-dibenzyltetrahydro-4H-furo[3, 4-d]imidazole-2, 4(1H)dione

The invention discloses an oxidation conversion method of 1, 3-dibenzyltetrahydro-4H-furo[3, 4-d]imidazole-2, 4(1H)dione. The method includes: mixing 1, 3-dibenzyltetrahydro-4H-furo[3, 4-d]imidazole-2, 4(1H)-dione, an alkaline reagent and water, carrying out hydrolysis reaction till dissolved clarification, thus obtaining a hydrolysate with a pH value of 8.0-10.0; then mixing the hydrolysate witha nitrogen oxide and an oxidizing reagent for oxidation reaction, and finally performing post-treatment to obtain cis1,3-dibenzylimidazole-2-one-4, 5-dicarboxylic acid. The one-step oxidation conversion method provided by the invention has the characteristics of mild reaction conditions, simple operation, environmental friendliness and low equipment requirement, and the obtained product has high yield and low production cost, therefore the method is very suitable for industrialization and sustainable production of biotin, and has great practical application value and social and economic benefits.

Synthesis method of biotin intermediate

The invention discloses a synthesis method of a biotin intermediate. The existing cyclic anhydride monoester compound is subjected to diastereomeric selective resolution by using a chiral resolving agent. The existing chiral resolving agent has the problems of high cost and low recovery reuse rate. According to the method provided by the invention, naphthenic acid is used as an initial raw material; the naphthenic acid is subjected to cyclization dewatering to prepare annular racemization carboxylic acid anhydride; reduction is performed to obtain racemization d,1-lactone; then, D-amino-compounds are used for resolution, so that a chiral product (4S,5R)-monoamide is separated out in a precipitate form; finally, acidolysis preparation is performed to obtain a biotin intermediate (3aS, 6aR)-lactone. The economic cheap and easy-to-recover and reuse D-amino-compounds are used as the preferred resolving agent; the reaction is simple; the post treatment is convenient; the cost is low; the pollution is little; all waste leftovers can be converted into the initial raw materials of naphthenic acid through oxidization; the goal of green, environment-friendly, economic and regenerated circulation reuse can be really achieved.

Desymmetric hydrogenation of a meso-cyclic acid anhydride toward biotin synthesis

Catalytic reactivity in the hydrogenation of a cyclic anhydride to a biotin synthetic intermediate has been investigated on the basis of Lyons' original method using Wilkinson Ru complex, revealing the high performance of DPPF and XANTPHOS diphosphines possessing wide bite angles. The results have shown a new trail for design of the corresponding asymmetric catalysts, and the potential utility of (S,S)-Et-FerroTANE and (S,S)-(R,R)-Ph-TRAP has been demonstrated.

An efficient and enantioselective synthesis of d-biotin

An efficient and enantioselective synthesis of d-biotin 1 starting from cis-1,3-dibenzyl-2-imidazo-lidone-4,5-dicarboxylic acid (6) is described. The key steps are the enantioselective reduction of meso-1,2-dicarboxylic thioanhydride 8 to prepare the (3as, 6ar)- thiolactone 9 and the introduction of the C6 side chain at C-2 in 9 via a modified Grignard reaction. This novel synthesis proceeded in six steps to afford 1 with 21% overall yield.

Method for the preparation of 1,3-disubstituted 4,5-cis-dicarboxy-2-imidazolidones

A process for the preparation of 1,3-disubstituted 4,5-cis-dicarboxy-2-imidazolidones useful as intermediates in the preparation of Vitamin H (biotin), said intermediates have the general formula STR1 in which R is an aliphatic hydrocarbon radical having 1 to 8 carbon atoms, an aralkyl radical or an aromatic hydrocarbon radical, preferably an allyl radical or a benzyl radical, comprising reacting a defined diaminosuccinic acid with phosgene in the presence of an alkali metal hydroxide.