Topiramate Azidosulfate

Base Information

• Chemical Name: Topiramate Azidosulfate
• CAS No.: 106881-35-0
• Molecular Formula: C12H19 N3 O8 S
• Molecular Weight: 365.364
• DSSTox Substance ID: DTXSID50549419
• Mol file: 106881-35-0.mol

Synonyms:Topiramate Azidosulfate;106881-35-0;[(1R,2S,6S,9R)-4,4,11,11-Tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl N-diazosulfamate;2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose azide sulphate;DTXSID50549419;W-200758;[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-2H,3aH,7H-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfurazidate (non-preferred name)

Chemical Property of Topiramate Azidosulfate

Chemical Property:

• PSA: 147.65000
• LogP: 1.48976
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 365.08928575
• Heavy Atom Count: 24
• Complexity: 668

Purity/Quality:

99%min. ^*data from raw suppliers

Topiramate Azidosulfate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2COC3(C(C2O1)OC(O3)(C)C)COS(=O)(=O)N=[N+]=[N-])C
• Isomeric SMILES: CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N=[N+]=[N-])C
• Uses: Topiramate (T540250) impurity.

Technology Process of Topiramate Azidosulfate

There total 3 articles about Topiramate Azidosulfate 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: 99.0%

topiramate (97240-79-4) → 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate (106881-35-0)

Guidance literature:

With fluorosulfonyl azide; potassium hydrogencarbonate; In tert-butyl methyl ether; water; N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

DOI:10.1038/s41586-019-1589-1

Reference yield:

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester (150609-95-3) → 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate (106881-35-0)

Guidance literature:

With pyridine; sodium azide; In acetonitrile; at 25 - 30 ℃; for 14h;

Reference yield:

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose (20880-92-6) → 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate (106881-35-0)

Guidance literature:

With pyridine; sodium azide; sulfuryl dichloride; Yield given. Multistep reaction; 1.) CH₂Cl₂, a) -15 deg C, 8 h, b) 23 deg C, 2 h, 2.) acetonitrile, 23 deg C, 18 h;

DOI:10.1021/jm00388a023

upstream raw materials:

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

topiramate

Downstream raw materials:

topiramate

Refernces

• 1、 -. "PROCESS AND PRODUCT". Page title page; 8-9. . Retrieved 2008/06/13.