26339-42-4

Basic information

• Product Name: (cis)-1,3-dibenzyldihydro-1H-furo[3,4-d]imidazole-2,4,6(3H)-trione
• Synonyms: (cis)-1,3-dibenzyldihydro-1H-furo[3,4-d]imidazole-2,4,6(3H)-trione;(cis)-1,3-Dibenzyldihydro-1H-furo(3,4-d)imidazol-2,4,6(3H)-trion;(3aα,6aα)-1,3-Dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4,6-trione;(3aβ,6aβ)-1,3-Dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4,6-trione;1,3-Dibenzyl-2,3,3aβ,4,6,6aβ-hexahydro-1H-furo[3,4-d]imidazole-2,4,6-trione;3aα,6aα-Dihydro-1,3-bis(phenylmethyl)-1H-furo[3,4-d]imidazole-2,4,6(3H)-trione;(4S,5R)-1,3-Dibenzyl-1H-furo[3,4-d]iMidazol-2,4,6-trione;cis-Dihydro-1,3-bis(phenylMethyl)-1H-furo[3,4-d]iMidazole-2,4,6(3H)-trione
• CAS NO: 26339-42-4
• Molecular Formula: C₁₉H₁₆N₂O₄
• Molecular Weight: 336.34134
• EINECS: 247-618-9
• Product Categories: Heterocyces;Aromatics;Biotin Derivatives;Aromatics, Biotin Derivatives, Heterocyces
• Mol File: 26339-42-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 236-237 °C
• Boiling Point: 597.3°Cat760mmHg
• Flash Point: 315°C
• Appearance: /
• Density: 1.388g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.652
• PKA: -1.25±0.20(Predicted)
• CAS DataBase Reference: (cis)-1,3-dibenzyldihydro-1H-furo[3,4-d]imidazole-2,4,6(3H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: (cis)-1,3-dibenzyldihydro-1H-furo[3,4-d]imidazole-2,4,6(3H)-trione(26339-42-4)
• EPA Substance Registry System: (cis)-1,3-dibenzyldihydro-1H-furo[3,4-d]imidazole-2,4,6(3H)-trione(26339-42-4)

Safety Data

• Hazardous Substances Data: 26339-42-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Biotin derivatives

InChI:InChI=1/C19H16N2O4/c22-17-15-16(18(23)25-17)21(12-14-9-5-2-6-10-14)19(24)20(15)11-13-7-3-1-4-8-13/h1-10,15-16H,11-12H2/t15-,16+

Upstream product

• 108-24-7 acetic anhydride 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 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 
• 28092-55-9 Acetic acid (3aR,4R,6aS)-1,3-dibenzyl-2,6-dioxo-hexahydro-furo[3,4-d]imidazol-4-yl ester 
• 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 

Downstream Products

• 28092-55-9 6ξ-acetoxy-1,3-dibenzyl-(3ar,6ac)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 96666-45-4 1,3-dibenzyl-5-(4-methoxybenzyl)-2,4,6-trioxopyrrolo<3,4-d>imidazoline 
• 26511-17-1 1,3,5-tribenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline 
• 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 
• 21035-81-4 (3aS)-1,3-dibenzyl-6ξ-hydroxy-(3ar,6ac)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 96666-48-7 1,3-dibenzyl-2,4,6-trioxopyrrolo<3,4-d>imidazoline 
• 148344-93-8 1,3-dibenzyl-5-hydroxy-2,4,6-trioxopyrrolo<3,4-d>imidazoline 
• 324012-37-5 cis-1,3-Dibenzyltetrahydro-2H-thieno[3,4-d]imidazole-2,4,6-trione 
• 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 
• 87637-48-7 (4R,5S)-1,3-dibenzyl-5-(methoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid 
• 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 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 

Relevant articles and documents

Practical Synthesis of (+)-Biotin Key Intermediate by Calcium Borohydride Reduction and Temperature-Dependent Purity Upgrade during Crystallization

An expedient synthesis of a key intermediate for (+)-biotin has been accomplished through high-yielding reduction of chiral imide with calcium borohydride and efficient isolation of the desired isomer by crystallization at a specific temperature where only undesired isomer was converted to soluble anhydrate while the desired isomer kept unchanged as a less soluble monohydrate.

Method for stereoselectively synthesizing chiral lactone, chiral compound and application of chiral compound

The invention relates to the field of organic synthesis, and discloses a method for stereoselectively synthesizing chiral lactone, a chiral compound and application of the chiral compound in synthesis of biotin. The method comprises the following steps: (1) carrying out first reaction on cyclic anhydride, cyclic chiral alcohol and organic alkali tertiary amine to obtain dicarboxylic acid mono-ester quaternary ammonium salt; (2) carrying out second reaction on the dicarboxylic acid mono-ester quaternary ammonium salt and a reducing agent after intermediate treatment or no intermediate treatment to obtain alcohol acid; and (3) under an acidic condition, carrying out a third reaction on the alcohol acid to obtain the chiral lactone shown in the formula (I). According to the method disclosed by the invention, the target product can be obtained with high selectivity and high yield.

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.