91780-38-0

Upstream product

• 91780-35-7 3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl chloride 
• 98933-74-5 tributyl-(3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexapyranosyl)stannane 
• 98933-74-5 tri-n-butyl-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)stannane 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

STEREOCONTROLLED PREPARATION OF C-2-DEOXY-α- AND -β-D-GLUCOPYRANOSYL COMPOUNDS FROM TRIBUTYL-(2-DEOXY-α- AND -β-D-GLUCOPYRANOSYL)STANNANES

Tributylstannyllithium treatment of 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl chloride (2) provided selectively tributyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranosyl)stannane (3) in 85percent yield.Isomeric tributyl (3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl)stannane (6) could be prepared in 70percent yield by reductive lithiation of 2 and reaction with tributyltin chloride.Tin-lithium exchange reaction, performed on 3 and 6 with butyllithium in oxolane at -78 deg C, generated the corresponding, configurationally stable 2-deoxy-β- and -α-D-hexopyranosyllithium compounds which reacted with electrophilic compounds with retention of configuration.Addition of these glycosyllithium reagnts to prochiral carbonyl compounds gave variable degrees of facial selectivity.A significant diastereofacial discrimination (10:1) was observed by condensation of 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyllithium reagent with hexanal and isobutyraldehyde.The structure of all C-glycopyranosyl compounds obtained was established by 1H-n.m.r. spectroscopy.

Stereospecific Generation of α- and β-Glycosyl-lithium Reagents from Glycosyl-stannanes: a Stereocontrolled Route to α- and β-C-Glycosides

Treatment of α- and β-D-tri-n-butylstannyl-glucopyranosides with n-butyl-lithium at -78 deg C generates configurationally stable α- and β-D-glycosyl-lithium species which accept electrophiles with retention of configuration.

Simple Generation of a Reactive Glycosyl-lithium Derivative

Two-step hydrolithiation of 3,4,6-tri-O-benzyl-D-glucal (hydrochlorination and lithium naphthalenide reductive lithiation) gives a reactive glycosyl-lithium derivative which is shown to be a precursor of C-glycosides.