133709-73-6

Basic information

• Product Name: trans 1,3-Dibenzyl-4-(hept-6'-enoyl)-5-hydroxymethylimidazolidine-2-one
• CAS NO: 133709-73-6
• Molecular Weight: 406.525
• Mol File: 133709-73-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: trans 1,3-Dibenzyl-4-(hept-6'-enoyl)-5-hydroxymethylimidazolidine-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: trans 1,3-Dibenzyl-4-(hept-6'-enoyl)-5-hydroxymethylimidazolidine-2-one(133709-73-6)
• EPA Substance Registry System: trans 1,3-Dibenzyl-4-(hept-6'-enoyl)-5-hydroxymethylimidazolidine-2-one(133709-73-6)

Safety Data

• Hazardous Substances Data: 133709-73-6(Hazardous Substances Data)

Upstream product

• 28092-62-8 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione 
• 2695-47-8 6-Bromo-1-hexene 

Relevant articles and documents

Biotin biosynthesis: Preparation of the postulated intermediate thiol

Previous work in our group led us to postulate thiol 3 as the first intermediate in the biotransformation of dethiobiotin 1 into biotin 2.A new synthesis of this thiol is described here starting from the lactone 4, an intermediate in the Hofmann La Roche industrial synthesis of biotin.After the failure of the Wittig approach, the side-chain was successfully introduced through a Grignard addition to the lactone followed by reduction of the ketone.Deoxygenation of the xanthate afforded the protected alcohol 29.To obtain the deprotected hydroxy acid 34a it was necessary to oxidize the double bond before the debenzylation of the imidazolidinone ring.The acid 34a was readily transformed into 3.Keywords: biotin / biosynthesis / alcohol deoxygenation / debenzylation