121804-01-1

Basic information

• Product Name: Ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside
• CAS NO: 121804-01-1
• Molecular Weight: 365.453
• Mol File: 121804-01-1.mol

Chemical Properties

• CAS DataBase Reference: Ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside(121804-01-1)
• EPA Substance Registry System: Ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside(121804-01-1)

Safety Data

• Hazardous Substances Data: 121804-01-1(Hazardous Substances Data)

Upstream product

• 117107-69-4 1,2-Di-O-acetyl-4-azido-4,6-dideoxy-3-O-benzyl-α-D-mannopyranoside 
• 75-08-1 ethanethiol 

Downstream Products

• 861819-35-4 ethyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-1-thio-β-D-glucopyranoside 
• 861819-33-2 ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside 
• 861819-34-3 ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-1-thio-β-D-glucopyranoside 
• 861819-36-5 ethyl 3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-1-thio-β-D-glucopyranoside 
• 861819-32-1 ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside 

Relevant articles and documents

Studies toward a conjugate vaccine for anthrax. Synthesis and characterization of anthrose [4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O- methyl-D-glucopyranose] and its methyl glycosides

The key step in the first chemical synthesis of anthrose (16) and its methyl α- (6) and β-glycoside (22) was inversion of configuration at C-2 in triflates 10, 2, and 18, respectively, obtained from the common intermediate, methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (1). To prepare methyl α-anthroside (6), methylation at O-2 of the gluco product 3, obtained from 2, was followed by hydrogenation/hydrogenolysis of the formed 2-methyl ether 4, to simultaneously remove the protecting benzyl group and reduce the azido function. Subsequent N-acylation of the formed amine 5 with 3-hydroxy-3-methylbutyric acid gave the target methyl α-glycoside 6. Synthesis of methyl β-anthroside (22) comprised the same sequence of reactions, starting from the known methyl 4-azido-3-O-benzyl-4,6-dideoxy-β- D-mannopyranoside (17), which was prepared from 1. In the synthesis of anthrose (16), 1-thio-β-glucoside 11, obtained from 1 through 10, was methylated at O-2, and the azido function in the resulting benzylated 1-thioglycoside 12 was selectively reduced to give amine 13. After N-acylation with 3-hydroxy-3-methylbutyric acid, 1-thioglycoside 14 was hydrolyzed to give the corresponding reducing sugar, aldol 15, which was debenzylated to afford anthrose.

Synthetic antigenic determinants of the Brucella A polysaccharide: A disaccharide thioglycoside for block synthesis of pentasaccharide and lower homologues of α1,2-linked 4,6-dideoxy-4-formamido-α-D-mannose

Methyl glycosides 13, 18, and 22, which represent potential antigenic determinants of the Brucella A polysaccharide, are the first synthetic analogues of this antigen.Their synthesis was necessitated by crystallographic studies of a Fab combining site obt