77611-19-9

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 133004-71-4 (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole 
• 75-05-8 acetonitrile 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 

Downstream Products

• 132884-68-5 N-<1-benzyl N-(tert-butyloxycarbonyl)-4-L-aspartyl>-2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine 
• 77611-20-2 Acetic acid (2R,3R,4S,5R,6R)-2-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 193154-32-4 Acetic acid (2R,3R,4S,5S,6S)-6-((2R,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-4,5-bis-benzyloxy-2-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents

Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.

Synthesis and biological evaluation of a backbone-modified phytoalexin elicitor

Two suitably protected building blocks (11 and 33) for the preparation of amide-linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal

Synthesis of N-Glycosides.Formation of Glucosylamine by Reaction of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose with Acetonitrile in the Presence of Trifluoromethanesulfonic Anhydride

The synthesis of glucosylamine by reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose with acetonitrile in the presence of trifluoromethanesulfonic anhydride was shown to proceed through an intermediate oxazoline.