154970-29-3

Upstream product

• 545-06-2 trichloroacetonitrile 
• 497096-15-8 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose 
• 136172-58-2 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose 
• 497096-14-7 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose 

Downstream Products

• 154918-93-1 methyl 2,3,4-tri-O-benzyl-6-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 176915-90-5 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(6-O-acetyl-2-azido-13,4-di-O-benzyl-2-deoxy-α-mannopyranosyl)-α-D-glucopyranoside 
• 154970-31-7 methyl 2,4-di-O-benzyl-3-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-6-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 154919-01-4 methyl 2,4-di-O-benzyl-3-O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-6-O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 154918-97-5 methyl 2,3,4-tri-O-benzyl-6-O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 154918-98-6 methyl 2,4-di-O-benzyl-6-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 176915-92-7 Acetic acid (2R,3S,4R,5S,6R)-5-azido-3,4-bis-benzyloxy-6-((2S,3R,4S,5R,6R)-4-benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 497096-21-6 2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-dibenzylphosphate-α-D-mannopyranoside 
• 497096-19-2 2-(benzyloxycarbonyl)aminoethyl 2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside 
• 497096-20-5 2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside 
• 497096-18-1 2-(benzyloxycarbonylamino)ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside 
• 154918-95-3 methyl 3-O-allyl-2,4-di-O-benzyl-6-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside 

Relevant academic research and scientific papers

Towards a synthetic glycoconjugate vaccine against Neisseria meningitidis A

Albumin conjugates of synthetic fragments of the capsular polysaccharide of the Gram-negative bacterium Neisseria meningitidis serogroup A were prepared. The fragments include monosaccharides 1 [α-D-ManpNAc-(1 → 30)-(CH2)2NH2] and 2 [6-O-P(O)-(O-)2-α-D-ManpNAc-(1 → O)-(CH2)2N-H2], disaccharide 3 {α-D-ManpNAc[1 → O-P(O)(O-) → 6]-α-D-ManpNAc(1 → O)-(CH2)2NH2}, and trisaccharide 4 {α-D-ManpNAc-[1 → O-P(O)(O-) → 6]-α-D-ManpNAc-[1 → O-P(O)(O-) → 6]-α-D-ManpNAc-(1 → O)-(CH2)2NH2}. Two monosaccharide blocks were employed as key intermediates. The reducing-end mannose unit featured the NHAc group at C-2, and contained the aminoethyl spacer as the aglycon for the final bioconjugation. The interresidual phosphodiester linkages were fashioned from an anomerically positioned H-phosphonate group in a 2-azido-mannose building block. The spacer-linked saccharides 1-4 were N-acylated with hepta-4,6-dienoic acid and the resulting conjugated diene-equipped saccharides were subjected to Diels-Alder-type addition with maleimidobutyryl-group functionalized human serum albumin to form covalent conjugates containing up to 26 saccharide haptens per albumin molecule. Complete 1H, 13C, and 31P NMR assignments for 1-4 are given. Antigenicity of the neoglycoconjugates containing 1-4 was demonstrated by a double immunodiffusion assay which indicated that a fragment as small as a monosaccharide is recognized by a polyclonal meningococcus group A antiserum and that the O-acetyl group(s) present in the natural capsular material is not essential for antigenicity.

SYNTHESIS OF MODIFIED DI- AND TRISACCHARIDE FRAGMENTS OF N-GLYCOPROTEINS

The syntheses of several analogues of disaccharide Manα(1->6)Manα-OCH3 (1) and of trisaccharide Manα(1->6)3)>Manα-OCH3 (2) are reported.The syntheses are described of the diastereomeric 6-methyl derivatives 9a and 9b, which are representatives o