6983-41-1

Basic information

• Product Name: 3-O-Benzoyl-5-deoxy-1-O,2-O-isopropylidene-β-L-threo-penta-4-enofuranose
• Synonyms: 3-O-Benzoyl-5-deoxy-1-O,2-O-isopropylidene-β-L-threo-penta-4-enofuranose
• CAS NO: 6983-41-1
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28454
• Mol File: 6983-41-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-O-Benzoyl-5-deoxy-1-O,2-O-isopropylidene-β-L-threo-penta-4-enofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-Benzoyl-5-deoxy-1-O,2-O-isopropylidene-β-L-threo-penta-4-enofuranose(6983-41-1)
• EPA Substance Registry System: 3-O-Benzoyl-5-deoxy-1-O,2-O-isopropylidene-β-L-threo-penta-4-enofuranose(6983-41-1)

Safety Data

• Hazardous Substances Data: 6983-41-1(Hazardous Substances Data)

Upstream product

• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 459839-20-4 3-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-D-ribofuranose 
• 50600-39-0 5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose 
• 84258-15-1 5-deoxy-5-iodo-1,2-O-isopropylidene-α-D-ribofuranose 

Relevant articles and documents

Synthesis of nucleosides from 4-methylidenefuranoses: A non-classical electrophilic addition

The reaction of persilylated bases (thymine, uracil, cytosine, and 5-fluorouracil) with either 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-erythro-pent-4-enofuranose 6 or its 3-O-benzyl analogue 7 in the presence of N-iodosuccinimide (NIS) afforded two types of product with high stereoselectivity; either (1′S,2′R,3′S)-3′-O-benzoyl- 8-10 or -3′-O-benzyl-5′-deoxy-5′-iodo-1′,2′-O- isopropylidene-4′-oxo-1′-yl-pyrimidines 11-13, respectively, from 1,4-addition with participation of the oxygen atom at the furanoid ring, and either 3′-O-benzoyl- 14-16, or 3′-O-benzyl-5′-deoxy-5′-iodo-1′,2′-O- isopropylidene-β-L-lyxo-4′-yl-pyrimidine and 17-19 resulting from normal electrophilic addition at the exocyclic methylene group. A third compound was isolated from the reaction of 7 with persilylated uracil/NIS and identified as the doubly N,N′-glycosylated pyrimidine 20.