26340-00-1

Usage

Uses

Used in Pharmaceutical Research:
.trans.-1,3-dibenzyl-dihydro-1H-furo[3,4-d]imidazole-2,4,6(3H)-trione is used as a compound of interest in pharmaceutical research due to its unique chemical structure and potential biological activity. Its specific application reason is the possibility of it being developed into a pharmaceutical agent, given its distinctive backbone and functional groups.
Used in Drug Development:
In the field of drug development, .trans.-1,3-dibenzyl-dihydro-1H-furo[3,4-d]imidazole-2,4,6(3H)-trione is used as a starting point for the design and synthesis of new drugs. The application reason is its potential to be modified and optimized to target specific biological pathways or receptors, which could lead to the creation of novel therapeutics.

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-/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 59564-78-2 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic 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 
• 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

• 28092-55-9 6ξ-acetoxy-1,3-dibenzyl-(3ar,6ac)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 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 

Relevant academic research and scientific papers

METHOD FOR PRODUCING AMIDE CARBOXYLIC ACID COMPOUND, AND METHOD FOR PRODUCING AMIDE ALCOHOL COMPOUND, AND METHOD FOR PRODUCING LACTONE COMPOUND

PROBLEM TO BE SOLVED: To provide a production method for efficiently obtaining a high-purity amide carboxylic acid compound, which is useful as a synthetic intermediate of biotin. SOLUTION: In a method for producing an amide carboxylic acid compound, an anhydride of a specific ureido compound is brought into contact with an optically active amine such as N-Me-R-α-methyl benzyl amine to obtain a mixture comprising an amide carboxylic acid compound, and then, the amide carboxylic acid compound is isolated from the obtained mixture. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

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.

Method for Producing Intermediate of Biotin and Method for Producing Biotin

In the method, a trione compound represented by the following formula (1) is (i) reduced by NaAlH2(OCH2CH2OCH3)2 and subsequently further reduced by a metal borohydride salt, or (ii) reduced by calcium borohydride, thereby producing an amide alcohol compound represented by the following formula (3) (wherein, R1 and R2 may be the same or different and each represents a hydrogen atom or a protecting group of an ureylene group; R4 represents an alkyl group, an aralkyl group, or an aryl group; and each of R5, R6, and R7 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom).

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.

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.

Highly enantioselective methanolysis of meso-cyclic anhydride mediated by bifunctional thiourea cinchona alkaloid derivatives: Access to asymmetric total synthesis of (+)-biotin

An enantioselective asymmetric total synthesis of (+)-biotin (1) via the Hoffmann-Roche lactone-thiolactone strategy has been accomplished from commercially available cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2). Strategic transformations include a cinchona alkaloid-based bifunctional thiourea mediated methanolytic desymmetrization of prochiral cyclic anhydride 3 to produce the enantiomerically enriched precursor of Roche lactone 5 and an improved introduction of the 4-carboxybutyl side chain at C-4 position of Roche thiolactone 6 via Grignard reaction.

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.

An improved asymmetric total synthesis of (+)-biotin via the enantioselective desymmetrization of a meso-cyclic anhydride mediated by cinchona alkaloid-based sulfonamide

The highly enantioselective total synthesis of (+)-biotin 1 via the Hoffmann-Roche lactone-thiolactone strategy has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid 2 with an overall yield of 35%. Two contiguous stereogenic centers at C-3a and C-6a were established through a rapid cinchona alkaloid-based sulfonamide-mediated enantioselective alcoholysis of meso-cyclic anhydride 3 to afford (4S,5R)-cinnamyl hemiester 4h, the direct precursor to (3aS,6aR)-lactone 5 with high enantioselectivity. A one-pot installation of the 4-carboxybutyl side chain was accomplished by a Fukuyama coupling reaction of (3aS,6aR)-thiolactone 6 with the organozinc reagent prepared from ethyl 5-bromopentanoate.