20881-80-5

Basic information

• Product Name: methyl 4-azido-4,6-dideoxymannopyranoside
• Synonyms: methyl 4-azido-4,6-dideoxymannopyranoside
• CAS NO: 20881-80-5
• Molecular Formula: C₇H₁₃N₃O₄
• Molecular Weight: 203.1958
• Mol File: 20881-80-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: methyl 4-azido-4,6-dideoxymannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-azido-4,6-dideoxymannopyranoside(20881-80-5)
• EPA Substance Registry System: methyl 4-azido-4,6-dideoxymannopyranoside(20881-80-5)

Safety Data

• Hazardous Substances Data: 20881-80-5(Hazardous Substances Data)

Usage

Description

Methyl 4-azido-4,6-dideoxymannopyranoside is a complex organic compound that serves as a key reactant in the preparation of various biologically significant molecules. It is characterized by its unique structure, which allows it to participate in crucial chemical reactions and contribute to the synthesis of important compounds in the fields of medicine and biology.

Uses

Used in Pharmaceutical Industry:
Methyl 4-azido-4,6-dideoxymannopyranoside is used as a reactant for the preparation of S-adenosyl-L-methionine enzyme, which can act as a deaminase or dehydrogenase depending on its sugar substrate. This enzyme plays a vital role in various biochemical processes, making it an essential component in the development of pharmaceuticals targeting specific metabolic pathways.
Used in Diagnostic Applications:
In the field of diagnostics, methyl 4-azido-4,6-dideoxymannopyranoside is used in the synthesis of a universal antigen to detect brucellosis, a bacterial infection that affects humans and animals. The compound's ability to contribute to the development of diagnostic tools highlights its importance in the medical field, as accurate and reliable detection of diseases is crucial for effective treatment and prevention strategies.

InChI:InChI=1/C7H13N3O4/c1-3-4(9-10-8)5(11)6(12)7(13-2)14-3/h3-7,11-12H,1-2H3/t3-,4-,5+,6+,7+/m1/s1

Downstream Products

• 20881-87-2 Methyl 4-amino-4,6-dideoxy-α-D-mannopyranoside 
• 115196-83-3 methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 121803-78-9 methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 121803-79-0 methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 116786-66-4 Methyl 4,6-Dideoxy-4-<(S)-2,4-dihydroxybutanamido>-α-D-mannopyranoside 
• 117107-69-4 1,2-Di-O-acetyl-4-azido-4,6-dideoxy-3-O-benzyl-α-D-mannopyranoside 
• 172603-68-8 (2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol 
• 134407-39-9 methyl O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 134407-44-6 methyl O-(2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 134407-40-2 methyl O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 134407-45-7 methyl O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 134407-42-4 methyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 134407-43-5 methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 

Relevant articles and documents

Synthetic explorations towards 3-deoxy-3-fluoro derivatives of D-perosamine

Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-α-D-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl 4-azido-2-O-benzyl-3,4,6-trideoxy-3-fluoro-α-D-altropyranoside. Treatment with DAST of methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-allopyranoside (8), or its 2-(p-methoxybenzyl) analog 9 resulted in fluorination with inversion of configuration at position 3, to give the corresponding 3-deoxy-3-fluoro glucopyranosides 10 and 11, respectively. Accordingly, compound 18 was prepared from 11, by de-p-methoxybenzylation at O-2, followed by inversion of configuration at C-2 in the resulting methyl 4-azido-3,4,6-trideoxy-3-fluoro-α-D-glucopyranoside. The 2-O-methyl analog of 18 (19) was prepared by methylation of 18. Compounds 18 and 19 were converted, conventionally, into the 3-fluoro analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1, serotype Inaba and Ogawa, respectively.