670249-21-5

Basic information

• Product Name: methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• Synonyms: methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• CAS NO: 670249-21-5
• Molecular Weight: 307.306
• Mol File: 670249-21-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside(670249-21-5)
• EPA Substance Registry System: methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside(670249-21-5)

Safety Data

• Hazardous Substances Data: 670249-21-5(Hazardous Substances Data)

Upstream product

• 4098-06-0 triacetyl-D-galactal 
• 196398-25-1 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α/β-D-galactopyranosyl nitrate 
• 68733-27-7 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl iodide 
• 67673-39-6 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 670249-18-0 methyl 2-azido-2-deoxy-α/β-D-galactopyranoside 

Downstream Products

• 1402224-14-9 methyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4-di-O-acetyl-6-О-chloroacetyl-β-D-glucopyranosyl-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 
• 1073182-55-4 methyl 6-O-benzoyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranoside 
• 1073182-16-7 methyl 2,3,4-tri-O-benzoyl-6-O-chloracetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 
• 258286-43-0 methyl 3-O-acetyl-2-azido-6-O-benzyl-2-desoxy-α-D-galactopyranoside 
• 893443-72-6 acetic acid 4,5-diacetoxy-2-[3-(4-acetoxy-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-5-azido-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy]-6-acetoxymethyl-tetrahydro-pyran-3-yl ester 
• 893443-74-8 (2R,3R,4S,5S,6R)-2-[(2S,3R,4R,5R,6R)-3-Azido-6-benzyloxymethyl-5-((2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 893443-59-9 Benzoic acid (2R,3R,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-4-acetoxy-5-azido-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 893443-61-3 Benzoic acid (2R,3R,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-5-azido-2-benzyloxymethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 893443-60-2 (2S,3R,4R,5R,6R)-3-Azido-6-benzyloxymethyl-2-methoxy-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-ol 
• 893443-63-5 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester 
• 893443-62-4 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,4aR,6S,7R,8R,8aR)-7-azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester 
• 894352-68-2 Acetic acid (2S,4aR,6S,7R,8R,8aR)-7-azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 

Relevant articles and documents

Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen

The first synthesis of the tumor-associated α-aminooxy T-antigen 1, a relevant recognition motif for the direct construction of multitopic carbohydrate architecture of biological interest is described. The usefulness of this building block is emphasized with the efficient preparation through oxime ligation of a neoglycopeptide cluster, which is readily suitable for evaluating the role of multivalency in antigen presentation to the immune system from an anticancer vaccine perspective.

Regioselective glycosylation of glucosamine and galactosamine derivates using O-pivaloyl galactosyl donors

Penta-O-pivaloyl-galactopyranose and tetra-O-pivaloyl-galactopyranosyl bromide after electrophilic activation reacted with 6-O-protected 2-azido-galactosides to give the precursor structures of the Thomsen-Friedenreich antigen disaccharide with high regioselectivity, but low yield. With 4,6-O-benzylidene protected 2-azidogalactosides and 2-O-pivaloyl phenylthio galactosides, T-antigen disaccharides of this type were obtained in good yields. Glycosylation reactions of 4,6-O-benzylidene protected glucosamine derivatives with O-pivaloyl protected galactosyl bromide efficiently gave lactolactosamine disaccharides. Even a thioglycoside was efficiently galactosylated by this method resulting in the formation of a disaccharide thioglycoside useful itself as a potential glycosyl donor.