628280-88-6

Upstream product

• 628280-98-8 allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 628280-91-1 allyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 628281-05-0 allyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 628281-06-1 allyl β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 628280-97-7 allyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 152432-87-6 allyl 2-azido-2-deoxy-α-D-glucopyranoside 
• 628281-08-3 allyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 952721-49-2 [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate 
• 727380-34-9 allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside 
• 727380-42-9 (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid 
• 727380-38-3 allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside 
• 628281-92-5 allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of glycosaminoglycan oligosaccharides - An unexpected inhibitory effect of a remote N-acetyl group upon trichloroacetimidate-mediated couplings

In order to prepare biologically relevant heparan sulfate (HS) tetrasaccharide fragments containing an N-acetylated glucosamine at the reducing end, we studied the glycosylation reaction between the 2-azidoglucose trichloroacetimidate disaccharide donor 1 and a range of 4′-OH-uronyl disaccharide acceptors with an N-acetylglucosamine at the reducing terminus. Although we tried several condensation conditions, no tetrasaccharide was formed. We show that the failure of these reactions is due to the presence of the N-acetyl group, which inhibits the trichloroacetimidate-mediated glycosylation, since the analogous reaction proceeds smoothly once the N-acetyl group has been replaced by an azide. In the latter case, we show that the careful optimisation of the solvent system is a powerful way to obtain high yields and α-stereoselectivity in coupling reactions of 1 with the 4-OH of a GlcUA acceptor. Thus, in a THF/Et2O (9:1) system, we obtained the GlcUA-β-(1→4)-GlcN3-α-(1→4)-GlcUA-β- (1→4)-GlcN3 tetrasaccharide 16α/β in 90% isolated yield and 92:8 α/β ratio, as compared to 57% yield and 70:30 α/β ratio when CH2Cl2 was used. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Efficient preparation of three building blocks for the synthesis of heparan sulfate fragments: Towards the combinatorial synthesis of oligosaccharides from hypervariable regions

New, multigram routes to suitably protected L-iduronyl monosaccharide donors 4 and 5 and 2-azidoglucose acceptors 6 and 7 are described. The L-iduronyl and D-glucuronyl disaccharides 1-3 were then prepared from these compounds, by means of efficient and regioselective protective group manipulations. These disaccharides form the basis of a combinatorial approach toward the synthesis of heparan sulfate fragments representative of the heterogeneous regions of this polysaccharide. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)Introduction.