863554-23-8

Upstream product

• 1613160-51-2 methyl 6-O-benzyl-3,4-O-isopropylidene-α-D-glucopyranoside 
• 20839-38-7 methyl 6-O-benzyl-α-D-glucopyranoside 
• 95188-91-3 methyl 2-O-allyl-4,6-O-benzylidene-α-D-altropyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 
• 863554-40-9 methyl 2-O-allyl 6-O-benzyl-3,4-O-isopropylidene-α-D-altropyranoside 
• 863554-21-6 methyl 2-O-allyl 6-O-benzyl-α-D-altropyranoside 
• 863554-22-7 methyl 6-O-benzyl-3,4-O-isopropylidene-α-D-altropyranoside 
• 863554-17-0 (3aR,4R,6S,7aR)-4-Benzyloxymethyl-6-methoxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one 

Downstream Products

• 863554-18-1 methyl 6-O-benzyl-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside 
• 863554-27-2 methyl 3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside 
• 863554-26-1 methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside 
• 863554-24-9 methyl 6-O-benzyl-3,4-O-isopropylidene-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside 

Relevant academic research and scientific papers

Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

We report a bio-inspired, strain driven epimerization of trans-ketals to cis-ketals through an enolate intermediate. Swern oxidation of a hydroxyl group adjacent to a trans-ketal effects both oxidation and its epimerization to cis-ketal. This novel and general strategy allows inversion of up to three contiguous stereocenters and has been illustrated by the synthesis of several unnatural/rare isomers of carbohydrates/cyclitols from their naturally abundant isomers. This journal is the Partner Organisations 2014.

Synthesis of the cyclopentyl nucleoside (-)-neplanocin A from D-glucose via zirconocene-mediated ring contraction

Two approaches for the conversion of D-glucose to (-)-neplanocin A (2), both based on the zirconocene-promoted ring contraction of a vinyl-substituted pyranoside, are herein evaluated (Scheme 1). In the first pathway (Scheme 1), the substrate possesses th