132203-12-4

Basic information

• Product Name: (+)-<3aS-(3α,4α,6aα)>-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno<3,4-d>imidazol-2(3H)-one
• Synonyms: (+)-<3aS-(3α,4α,6aα)>-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno<3,4-d>imidazol-2(3H)-one
• CAS NO: 132203-12-4
• Molecular Weight: 340.446
• Mol File: 132203-12-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (+)-<3aS-(3α,4α,6aα)>-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno<3,4-d>imidazol-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-<3aS-(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)
• EPA Substance Registry System: (+)-<3aS-(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)

Safety Data

• Hazardous Substances Data: 132203-12-4(Hazardous Substances Data)

Upstream product

• 103621-13-2 (+/-)-(3aα,4α,6aα)-4-Chlorotetrahydro-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 56198-34-6 (3aα,6aα)-1,3-dibenzylhexahydro-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>-<3aS-(3aα,4α,6aα)>-tetrahydro-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 132203-10-2 Methyl (S)-α-<<3aS-(3aα,4α,6aα)>-2-hexahydro-2-oxo-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-4-yloxy>benzeneacetate 
• 132203-11-3 (S)-α-<<3aS-(3aα,4α,6aα)>-2-Hexahydro-2-oxo-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-4-yloxy>benzeneacetic acid 
• 132203-08-8 4-<(S)-1-Phenylethoxy>-<3aS-(3aα,4α,6aα)>-tetrahydro-1,3-bis(phenylmethyl)-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 
• 103621-13-2 (+)-(3aα,4α,6aα)-4-Chlorotetrahydro-1,3-bis(phenylmethyl)-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 
• 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 

Relevant articles and documents

An Efficient Method for the Resolution of Key Intermediate to D-Biotin via Chiral Amines

An efficient method for the resolution of key intermediate to D-biotin in high chemical and optical yields is reported.

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.

Synthesis of (+)-biotin: Efficient resolution of key intermediates

Enantiomerically pure 4-chlorothieno[3,4-d]imidazol-2-one (+)-2 and thieno[3,4-d]imidazol-2,4-dione (+)-5, key intermediates in independent routes to (+)-biotin (6), have been prepared by resolution via the corresponding diastereomeric ethers (3d-g and 3'd-g). Efficient procedures to recycle the undesired diastereomers and recover the chiral auxiliary have been developed.