122992-59-0

Basic information

• Product Name: (2,3-di-O-benzyl-β-D-glucopyranosyl)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
• Synonyms: (2,3-di-O-benzyl-β-D-glucopyranosyl)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
• CAS NO: 122992-59-0
• Molecular Weight: 619.671
• Mol File: 122992-59-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2,3-di-O-benzyl-β-D-glucopyranosyl)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: (2,3-di-O-benzyl-β-D-glucopyranosyl)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose(122992-59-0)
• EPA Substance Registry System: (2,3-di-O-benzyl-β-D-glucopyranosyl)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose(122992-59-0)

Safety Data

• Hazardous Substances Data: 122992-59-0(Hazardous Substances Data)

Upstream product

• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 55682-57-0 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 796873-51-3 β-D-glucopyranosyl-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 1379585-58-6 (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 1379585-57-5 (4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 122992-58-9 (4aR,6S,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7,8-bis-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine 

Downstream Products

• 1379585-66-6 (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 122992-60-3 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((1R,2S,3R,4R,5R)-4-azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl ester 
• 104616-12-8 1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-levulinyl-β-D-glucopyranosyluronate)-D-glucopyranose 
• 104616-13-9 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronato)-α-D-glucopyranosyl bromide 
• 104616-10-6 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronato)-α-D-glucopyranose 
• 123012-49-7 (2R,3R,4S,5R,6S)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-ol 

Relevant articles and documents

Investigating glycol-split-heparin-derived inhibitors of heparanase: A study of synthetic trisaccharides

Heparanase is the only known endoglycosidase able to cleave heparan sulfate. Roneparstat and necuparanib, heparanase inhibitors obtained from heparin and currently being tested in man as a potential drugs against cancer, contain in their structure glycol-split uronic acid moieties probably responsible for their strong inhibitory activity. We describe here the total chemical synthesis of the trisaccharide GlcNS6S-GlcA-1,6anGlcNS (1) and its glycol-split (gs) counterpart GlcNS6S-gsGlcA-1,6anGlcNS (2) from glucose. As expected, in a heparanase inhibition assay, compound 2 is one order of magnitude more potent than 1. Using molecular modeling techniques we have created a 3D model of 1 and 2 that has been validated by NOESY NMR experiments. The pure synthetic oligosaccharides have allowed the first in depth study of the conformation of a glycol-split glucuronic acid. Introducing a glycol-split unit in the structure of 1 increases the conformational flexibility and shortens the distance between the two glucosamine motives, thus promoting interaction with heparanase. However, comparing the relative activities of 2 and roneparstat, we can conclude that the glycol-split motive is not the only determinant of the strong inhibitory effect of roneparstat.

Synthesis of several sulphated and non-sulphated pentasaccharides, corresponding to the E. coli K5 glycosaminoglycan

The synthesis is described of four pentasaccharides, which are structurally related to the bacterial capsular polysaccharide isolated from E. coli K5 (010/K5/H40), i.e. the so-called K5 antigen.These four synthetic compounds comprise: (i) a pentasaccharide that is structurally identical to the K5 antigen (i.e. compound 16); (ii, iii) two pentasaccharides containing two and three O-sulphated groups respectively on defined positions (i.e. compounds 15a and 15b); (iv) a pentasaccharide that is O-sulphated on all hydroxyl groups (i.e. compound 17).These four K5-antigen-related pentasaccharides were synthesized from the fully protected pentasaccharides 13a and 13b.The preparation of compounds 13a,b was based on coupling of disaccharide 6a with the disaccharide 10a or 10b to give tetrasaccharides 11a,c, respectively, which in turn were coupled to monosaccharide 12.Deblocking of the pentasaccharides 13a,b and conversion into the pentasaccharides 15a and 15b was performed by saponification of the ester functions, O-sulphation, hydrogenalysis and finally selective N-acetylation. compound 16 was obtained from 13a,b by saponification of the ester functions, deblocking of the benzyl and N-protective groups, followed by selective N-acetylation.The persulphated derivative 17 was obtained from 15a by extensive O-sulphation.The structure of the K5-antigen-related pentamers was confirmed by 1H NMR- and 13C NMR-spectroscopical techniques.