104016-91-3

Upstream product

• 88580-20-5 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranosyl chloride 
• 151767-37-2 thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside 
• 2873-29-2 D-glucal triacetate 
• 104017-13-2 (2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran 
• 100-52-7 benzaldehyde 
• 515821-31-5 phenylsulfonyl 3,4,6-tri-O-butyldimethylsilyl-2-deoxy-α,β-D-arabino-hexopyranoside 

Downstream Products

• 104016-96-8 [(2R,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-phenyl-methanone 
• 104017-04-1 [(2S,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-phenyl-methanone 

Relevant academic research and scientific papers

Preparation and reductive lithiation of 2-deoxy-D-glucopyranosyl phenylsulfones: A highly stereoselective route to C-glycosides

2-Deoxy-D-glucopyranosyl phenylsulfones 3a-c have been synthesized in 75-83% yield from commercial tri-O-acetyl-D-glucal 1. Their reductive desulfonylation by lithium naphthalenide and reaction of the intermediate glycosyl-lithium 5 with aldehydes leads t

D-GLUCOPYRANOSYL PHENYLSULFONES: THEIR USE IN A STEREOCONTROLLED SYNTHESIS OF CIS 2,6-DISUBSTITUTED TETRAHYDROPYRANS (β-D-C-GLYCOSIDES)

The lithiated anion derived from 3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α,β-D-glucopyranosyl phenylsulfones 1 reacts with various electrophiles leading to alkylated products, precursors of β-D-C-glycosides 5a-g after stereocontrolled desulfonylation and