568579-45-3

Upstream product

• 23202-83-7 5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 79-08-3 bromoacetic acid 
• 100-39-0 benzyl bromide 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 532-20-7 α-D-xylofuranose 

Downstream Products

• 568579-46-4 (R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Relevant academic research and scientific papers

An asymmetric Kharasch reaction mediated by D-xylose: Long range diastereocontrol

An asymmetric Kharasch-type atom transfer reaction was studied under 13 different sets of reaction conditions in order to obtain the highest levels of diastereoselection. The highest ratio of 12.5:1 (71%) was observed at low temperatures (-78°C) using the Lewis acid Eu(OTf)3. Because the new asymmetric center is so distant from the D-xylose, we propose a transition state involving two sugars. The conversion of the major product to a naturally occurring chiral γ-butyrolactone, under basic conditions, is described which also confirmed the diastereoselectivity and absolute stereochemistry of the Kharasch reaction.