Methyl 4-azido-4,6-dideoxymannopyranoside

Base Information

• Chemical Name: Methyl 4-azido-4,6-dideoxymannopyranoside
• CAS No.: 20881-80-5
• Molecular Formula: C7H13N3O4
• Molecular Weight: 203.198
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID00174997
• Wikidata: Q83045197
• Mol file: 20881-80-5.mol

Synonyms:M-4-ADM;methyl 4-azido-4,6-dideoxy-alpha-D-mannopyranoside;methyl 4-azido-4,6-dideoxymannopyranoside

Chemical Property of Methyl 4-azido-4,6-dideoxymannopyranoside

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 108.67000
• Density: g/cm³
• LogP: -0.76894
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 203.09060590
• Heavy Atom Count: 14
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-Azido-4,6-dideoxy-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC)O)O)N=[N+]=[N-]
• Isomeric SMILES: C[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC)O)O)N=[N+]=[N-]
• Uses: is a reactant in the preparation of S-adenosyl-L-methionine enzyme which can act as a deaminase or dehydrogenase depending on it’s sugar substrate. Also used in the synthesis of a universal antigen to detect brucellosis

Technology Process of Methyl 4-azido-4,6-dideoxymannopyranoside

There total 1 articles about Methyl 4-azido-4,6-dideoxymannopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-arabino-hexopyranosid-3-ulose → (2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol (20881-80-5) + methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-allopyranoside (381168-02-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; water; for 1h;

DOI:10.1016/S0008-6215(01)00188-4

Reference yield: 97.0%

(2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol (20881-80-5) + benzyl bromide (100-39-0) → methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (121803-79-0)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(94)00319-B

Reference yield: 97.0%

(2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol (20881-80-5) + benzoyl chloride (98-88-4) → methyl 4-azido-2,3-di-O-benzoyl-4,6-dideoxy-α-D-mannopyranoside

Guidance literature:

With pyridine; dmap; at 0 - 21 ℃; for 10h; Inert atmosphere;

DOI:10.1021/ja5081184

Downstream raw materials:

Methyl 4-amino-4,6-dideoxy-α-D-mannopyranoside

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-mannopyranoside