21035-77-8

Basic information

• Product Name: 2,4-dibenzyl-6-hydroxy-7-thia-2,4-diaza-bicyclo[3.3.0]octan-3-one
• Synonyms: 2,4-dibenzyl-6-hydroxy-7-thia-2,4-diaza-bicyclo[3.3.0]octan-3-one
• CAS NO: 21035-77-8
• Molecular Weight: 340.446
• Mol File: 21035-77-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,4-dibenzyl-6-hydroxy-7-thia-2,4-diaza-bicyclo[3.3.0]octan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dibenzyl-6-hydroxy-7-thia-2,4-diaza-bicyclo[3.3.0]octan-3-one(21035-77-8)
• EPA Substance Registry System: 2,4-dibenzyl-6-hydroxy-7-thia-2,4-diaza-bicyclo[3.3.0]octan-3-one(21035-77-8)

Safety Data

• Hazardous Substances Data: 21035-77-8(Hazardous Substances Data)

Upstream product

• 56198-34-6 (3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 103621-13-2 (+/-)-(3aα,4α,6aα)-4-Chlorotetrahydro-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 7677-24-9 trimethylsilyl cyanide 
• 21035-77-8 (+/-)-(3aα,4α,6aα)-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 132150-93-7 4-<(3β,5α)-Cholestan-3-yloxy>-<3aR-(3aα,4α,6aα)>-tetrahydro-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 132150-94-8 Methyl (S)-α-<<3aR-(3aα,4α,6aα)>-2-hexahydro-2-oxo-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-4-yloxy>benzeneacetate 
• 132150-95-9 (S)-α-<<3aR-(3aα,4α,6aα)>-2-Hexahydro-2-oxo-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-4-yloxy>benzeneacetic acid 
• 132150-92-6 4-<(S)-1-Phenylethoxy>-<3aR-(3aα,4α,6aα)>-tetrahydro-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-2(3H)-one 

Downstream Products

• 56198-34-6 (3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 21035-72-3 (3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>-imidazole-2(3H),4-dione 
• 21035-77-8 <3aR-(3α,4α,6aα)>-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 132203-12-4 (+)-<3aS-(3α,4α,6aα)>-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 

Relevant articles and documents

SYNTHESIS OF A KEY INTERMEDIATE FOR D-BIOTIN VIA 1,3-CYCLOADDITION OF A THIOCARBONYL YLIDE AND SILA PUMMERER REARRANGEMENT

An efficient preparation of a d-biotin intermediate, (+/-)-(3aα,4α,6aα)-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thienoimidazol-2(3H)-one was accomplished by use of 1,3-cycloaddition of a thiocarbonyl ylide, Curtius rearrangement and sila-Pum

Synthesis of d-Biotin Chiral Intermediates via a Biochemical Method

The enzyme-catalyzed kinetic resolution of (+/-)-(3aα,4α,6aα)-4-acetoxy-1,3-dibenzyl-3a,4,6,6a-tetrahydro-1H-thienoimidazol-2(3H)-one was examined.Lipase B from Pseudomonas fragi and rabbit liver esterase gave (-)--1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thienoimidazol-2(3H)-one , while Streptomyces rochei var. volubilis gave the alcohol (S)-(2), which is a key intermediate in the synthesis of d-biotin, with high enantioselectivity.

Nucleophilic Displacements on an α-Chloro Thioether by Organocuprates: A Novel Synthesis of Desoxybiotin

Reactions of organometallic reagents with α-chloro thioether 2, which is readily prepared from thienoimidazolone 1, have been investigated as an approach to the synthesis of biotin (10).Methyllithium and methylmagnesium bromide attack exclusively from the less hindered exo face, affording 4, while lithium dimethylcuprate attacks from the endo face with inversion of configuration, affording 5.Lithium dipentylcuprate affords predominantly exo isomer 6, while halide-free lithium methylpentylcuprate affords predominantly endo isomer 7.Debenzylation of 7 yields desoxybiotin (9) which can be microbially oxidized to biotin (10).Alternatively, 2 was hydrolyzed and oxidized to thiolactone 13, a known precursor of biotin.