628281-92-5

Upstream product

• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 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 
• 1450734-54-9 4-methoxybenzyl N-phenyl-2,2,2-trifluoroacetimidate 
• 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 
• 105-13-5 4-Methoxybenzyl alcohol 
• 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 
• 628280-98-8 allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-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 
• 628280-88-6 allyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-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

• 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 
• 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 
• 1624284-89-4 3-[(3-benzyloxycarbonylamino)propylthio]propyl (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 
• 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 

Relevant academic research and scientific papers

P-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: A versatile reagent for mild acid catalyzed etherification

PMB-NPTFA 1a is a new month bench stable and powerful reagent for the formation of PMB ethers. Several alcohols were protected in high yields and short reaction times, using low reagent loading and small catalytic amounts of Bi(OTf)3. The mild

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.