104616-10-6

Basic information

• Product Name: 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
• CAS NO: 104616-10-6
• Molecular Weight: 745.783
• Mol File: 104616-10-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(104616-10-6)
• EPA Substance Registry System: 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(104616-10-6)

Safety Data

• Hazardous Substances Data: 104616-10-6(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 55682-57-0 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 104616-11-7 methyl (2,3-di-O-benzyl-4-O-levulinyl-α-D-glucopyranosyl bromide)uronate 
• 126684-06-8 methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-levulinyl-α-D-glucopyranosid)uronate 
• 118282-21-6 methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranuronate 
• 87326-44-1 methyl (prop-1-enyl 2,3-di-O-benzyl-α-D-glucopyranosid)uronate 
• 123-76-2 levulinic acid 
• 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 
• 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 
• 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 
• 122992-59-0 (2,3-di-O-benzyl-β-D-glucopyranosyl)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 40608-06-8 levulinic anhydride 
• 100-39-0 benzyl bromide 

Downstream Products

• 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 
• 104616-12-8 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 

Relevant articles and documents

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.