87585-00-0

Upstream product

• 28092-55-9 6ξ-acetoxy-1,3-dibenzyl-(3ar,6ac)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 26339-42-4 (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 40222-70-6 1,3-dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid anhydride 
• 21035-81-4 1,3-dibenzyl-6-hydroxy-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 40222-71-7 cis-1,3-dibenzyl-hexahydro-1H-furo[3,4-d]imidazole-2,4-dione 
• 157378-76-2 C₁₉H₂₀N₂O₄ 
• 95790-95-7 Acetic acid (4S,5R)-1,3-dibenzyl-5-hydroxymethyl-2-oxo-imidazolidin-4-ylmethyl ester 
• 83889-74-1 (4S,5R)-1,3-Dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid dipropyl ester 
• 83889-76-3 (4S,5R)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid 

Downstream Products

• 171232-73-8 (+)-cis-1,3-dibenzylhexahydro-1H-thieno-[3,4-d]imidazole-2,4-dione 
• 21035-72-3 (+)-cis-1,3-dibenzyl-hexahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 40222-71-7 cis-1,3-dibenzyl-hexahydro-1H-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 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 

Relevant academic research and scientific papers

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.

A NEW CHIRAL BIPHENYL DIPHOSPHINE LIGAND AND PROCESS FOR PREPARATION THEREOF

The present invention is related to a new chiral biphenyl diphosphine ligand of formula (I), wherein R1, R2, and R3 are independently H, alkyl or aryl; R6 and R7 is independently a substituent; and A is independently aryl or heteroaryl, optionally substituted by one or more substituents, or a stereoisomer thereof, or a stereoisomeric mixture thereof.

Method for synthesizing optical pure biotin intermediate lactone

The invention relates to a method for preparing optical pure biotin intermediate lactone II through catalytic desymmetrisation reduction of anhydride I. According to the method, the biotin intermediate anhydride I is used as a reaction substrate; under the catalysis effect of transmission metal, the optical pure biotin intermediate lactone II is prepared. Compared with a conventional method, the method provided by the invention has the characteristics that the catalyst consumption is low; the conversion rate is high; the ee value is high; the cost is low; the operation is simple; the green and environment-friendly effects are achieved. The method is suitable for large-scale industrial production.

Catalytic enantioselective desymmetrization of meso cyclic anhydrides via iridium-catalyzed hydrogenation

A novel method to desymmetrize meso-anhydrides into lactones via asymmetric hydrogenation catalyzed by the Ir-C3*-TunePhos complex has been developed. Various chiral lactones were synthesized with full conversion and excellent enantioselectivit

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.

Synthesis of dendrimer-type chiral stationary phases based on the selector of (1S,2R)-(+)-2-amino-1,2-diphenylethanol derivate and their enantioseparation evaluation by HPLC

In our recent work, a series of dendritic chiral stationary phases (CSPs) were synthesized, in which the chiral selector was L-2-(p-toluenesulfonamido)-3- phenylpropionyl chloride (selector I), and the CSP derived from three-generation dendrimer showed the best separation ability. To further investigate the influence of the structures of dendrimer and chiral selector on enantioseparation ability, in this work, another series CSPs (CSPs 1-4) were prepared by immobilizing (1S,2R)-1,2-diphenyl-2-(3-phenylureido)ethyl 4-isocyanatophenylcarbamate (selector II) on one- to four-generation dendrimers that were prepared in previous work. CSPs 1 and 4 demonstrated the equivalent enantioseparation ability. CSPs 2 and 3 showed the best and poorest enantioseparation ability respectively. Basically, these two series of CSPs exhibited the equivalent enantioseparation ability although the chiral selectors were different. Considering the enantioseparation ability of the CSP derived from aminated silica gel and selector II is much better than that of the one derived from aminated silica gel and selector I, it is believed that the dendrimer conformation essentially impacts enantioseparation.

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.

A formal catalytic asymmetric synthesis of (+)-biotin with modified cinchona alkaloids

A formal catalytic asymmetric synthesis of (+)-biotin was realized. The key steps involve a catalytic, highly enantioselective and quantitative desymmetrization of a meso cyclic anhydride followed by a one-pot chemoselective reduction to form the optically active lactone intermediate in the Goldberg - Sternbach (+)-biotin synthesis.

Stereocontrol in the reduction of meso-imides using oxazaborolidine, leading to a facile synthesis of (+)-deoxybiotin

Highly enantioselective reduction of meso-imides was conducted using oxazaborolidine derived from L-threonine and borane-THF complex to give lactams in high enantiomeric purity. This methodology was successfully applied to the synthesis of (+)-deoxybiotin

Highly enantioselective reduction of meso-1,2-dicarboxylic anhydrides

Optically active lactones (2a-2g) were synthesized by highly enantioselective reduction of readily available meso-1,2-dicarboxylic anhydrides (1a-1g) using lithium aluminum hydride-ethanol-1,1'-bi-2-naphthol complex (BINAL-H).