94530-17-3

Upstream product

• 94530-15-1 6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-trifluoromethylsulphonyl-α-D-xylo-hexofuranose 
• 94530-12-8 3,5-dideoxy-1,2-O-isopropylidene-α-D-glycero-hex-4-enofuranose 
• 7284-07-3 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 
• 94530-14-0 6-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 74152-55-9 5-deoxy-1,2-O-isopropylidene-3-(1-methoxy-1-methyl ethyl)-α-D-xylo-hexofuranose 
• 100-39-0 benzyl bromide 
• 94530-16-2 6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-glycero-hex-3-enofuranose 
• 94530-13-9 6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-glycero-hex-4-enofuranose 

Downstream Products

• 94530-20-8 (R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one 
• 94530-19-5 (S)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one benzoate 

Relevant academic research and scientific papers

A Concise And General Entry into (R)-4-Hydroxy-2-Substituted Cyclopent-2-enones from D-Glucose: Chiral Intermediates for the Synthesis of PGE2, (-)-Pentenomycin I, and Allethrin

A general strategy for the transformation of D-glucose into different (R)-4-hydroxycyclopent-2-enones is described.This has been illustrated by the synthesis of (R)-2--4-hydroxycyclopent-2-enone, (R)-2-benzyloxymethyl-4-hydroxycyclopent-2-enone, and (R)-2-allyl-4-hydroxycyclopent-2-enone, which are potential chiral synthons for prostaglandin E2, the antibiotic (-)-pentenomycin I, and the synthetic insecticide allethrin, respectively.The second chiral synthon was obtained by two different routes, one of them involving a novel palladium(0)-catalysed rearrangement of a vinyloxirane intermediate.

Synthesis of (R)-4-Hydroxy-2-benzyloxymethylcyclopent-2-en-1-one from D-Glucose via Palladium(0)-catalysed Rearrangement of a Vinylic Epoxide Intermediate

The transformation of D-glucose into (R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one (3), a potential chiral synthon for the antibiotic (-)-pentenomycin I (4), has been achieved via the intramolecular aldolisation-dehydration of the 2-hydroxy-4-oxo-aldehyde (9) which was obtained by two different routes, one of them involving palladium(0)-catalysed rearrangement of a vinylic epoxide intermediate.