79297-67-9

Upstream product

• 141019-76-3 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-phenoxythiocarbonyl-α-D-glucopyranoside 
• 79233-82-2 Imidazole-1-carbothioic acid O-((2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl) ester 
• 78246-81-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 58006-39-6 benzyl 2-acetamido-2,3-dideoxy-α-D-ribo-hexopyranoside 
• 131473-45-5 benzyl 2-acetamido-4,6-di-O-acetyl-2,3-dideoxy-α-D-ribo-hexopyranoside 
• 131473-47-7 2-acetamido-4,6-di-O-acetyl-2,3-dideoxy-α-D-ribo-hexopyranosyl dibenzyl phosphate 

Relevant academic research and scientific papers

Combined chemical-enzymic synthesis of deoxygenated oligosaccharide analogs: transfer of deoxygenated D-GlcpNAc residues from their UDP-GlcpNAc derivatives using N-acetylglucosaminyltransferase I

The 3"-,4"-, and 6"-deoxy analogs of UDP-GlcpNAc have been synthesized chemically and found to act as donor-substrates for N-acetylglucosaminyltransferase-I (GnT-I) from human milk.Incubation of UDP-GlcpNAc and these deoxy analogs with GnT-I in the presence of α-D-Manp-(1->3)-6)>-β-D-Manp-O(CH2)8COOMe gave β-D-GlcpNAc-(1->2)-α-D-Manp-(1->3)-6)>-β-D-Manp-O(CH2)8COOMe(6), and the deoxy analogs 12-14 where HO-3, HO-4, and HO-6, respectively, of the β-D-GlcNAc residue were replaced by hydrogen.The tetrasaccharide glycosides 6 and 12-14 were characterized by 1H-n.m.r. spectroscopy and evaluated as acceptors for GnT-II, the next enzyme in the pathway of biosynthesis of Asn-linked oligosaccharides.Deoxygenation of the 3-position of the β-D-GlcNAc residue of 6 completely abolished its acceptor activity, whereas removal of HO-4 or HO-6 caused only modest decreases in activity.

Further Aspects of the Reduction of Dithiocarbonates with Tributyltin Hydride and Deuteride

The reduction of 1,2:5,6-di-O-isopropylidene-3-O-(methylthio)thiocarbonyl-β-D-idose, -talose, and -(3-(2H))talose with tributyltin hydride and deuteride leads to the deoxy sugar and some deuteriumcontaining deoxy sugars.A modification of the normal procedure allows for reduction with tributyltin hydride generated in situ.As well, the reduction of some dithiocarbonates derived from glycosides of N-acetyl-D-glucosamine allows to a variety of dideoxy and trideoxy sugars.

Synthesis of Deoxy Sugars. Deoxygenation by Treatment with N,N'-Thiocarbonyldiimidazole/Tri-n-butylstannane

Protected sugars containing a free hydroxyl group have been deoxygenated by conversion to the O-(imidazolylthiocarbonyl) derivative with N,N'-thiocarbonyldiimidazole followed by treatment with tri-n-butylstannane.This reaction sequence offers a mild, high-yield procedure for the deoxygenation of hexose derivatives with a hindered secondary hydroxyl group at C-3 or C-4.The primary 6-O-(imidazolylthiocarbonyl) compound obtained from 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose reacts with tri-n-butylstannane to give a mixture of the 6-deoxy sugar (31percent) and starting alcohol (57percent).