178812-81-2

Basic information

• Product Name: methyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside
• Synonyms: methyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside
• CAS NO: 178812-81-2
• Molecular Weight: 281.352
• Mol File: 178812-81-2.mol

Chemical Properties

• CAS DataBase Reference: methyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside(178812-81-2)
• EPA Substance Registry System: methyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside(178812-81-2)

Safety Data

• Hazardous Substances Data: 178812-81-2(Hazardous Substances Data)

Upstream product

• 115196-83-3 methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 172603-65-5 methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 

Downstream Products

• 208580-03-4 methyl 3-O-benzoyl-4-(2-O-benzoyl-4-tert-butyldiphenylsilyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 
• 208580-00-1 methyl 3-O-imidazoylthiocarbonyl-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 
• 208579-98-0 methyl 3-O-benzyl-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycerotetronamido)-2-O-methyl-α-D-mannopyranoside 
• 208580-05-6 methyl 3-O-benzoyl-4-(4-O-benzoyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 
• 208580-02-3 (S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-N-((2R,3S,4S,5S,6S)-4-hydroxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-butyramide 
• 208579-99-1 methyl 4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside 
• 208580-01-2 methyl 3,4,6-trideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside 
• 208580-08-9 (S)-2-Benzyloxy-N-((2R,3R,4S,5S,6S)-4-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-4-chloro-butyramide 
• 208580-07-8 (S)-2-Benzyloxy-N-((2R,3R,4S,5S,6S)-4-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-4-hydroxy-butyramide 
• 208579-97-9 (S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide 

Relevant articles and documents

Synthesis of terminal disaccharide elements corresponding to the Ogawa and Inaba antigenic determinant from Vibrio cholerae O1

Vibrio cholerae O1 LPS terminal mono- and disaccharide elements were synthesized by reduction of the azido group in several 4-amino-4,6-dideoxy- D-mannose mono- and disaccharide derivatives, followed by coupling with 2,4- di-O-acetyl-3-deoxy-L-glycero-tetronic acid in the presence of 2-ethoxy-l- ethoxycarbonyl-1,2-dihydroquinoline. This compound represents a useful model in order to elucidate the size of the epitopes which define Ogawa and Inaba serotypes from Vibrio cholerae O1.

Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa

Methyl 4-azido-4,6-dideoxy-3-O-benzyl-α-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside.Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetranamido)-2-O-methyl-α-D-mannopyranose, the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa.The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group.The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae O:1; serotype Inaba.The crystal structure of methyl 4,6-dideoxy-2-O-methyl-4-trifluoroacetamido-α-D-mannopyranoside is also described.Keywords: O-Polysaccharide; Vibrio cholerae O:1, serotype Ogawa; α-D-Mannopyranoside, methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-teronamido)-2-O-methyl; Synthesis; Antigenic determinant