4,5-Desisopropylidene Topiramate

Base Information

• Chemical Name: 4,5-Desisopropylidene Topiramate
• CAS No.: 106881-41-8
• Molecular Formula: C9H17 N O8 S
• Molecular Weight: 299.302
• UNII: 0KP2WFO28K
• DSSTox Substance ID: DTXSID90442617
• Nikkaji Number: J3.496.477G
• Wikidata: Q82259990
• Mol file: 106881-41-8.mol

Synonyms:4,5-Desisopropylidene Topiramate;106881-41-8;4,5-Diol-topiramate;0KP2WFO28K;[(3aS,6R,7R,7aS)-6,7-dihydroxy-2,2-dimethyl-5,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-b]pyran-3a-yl]methyl sulfamate;2,3-O-(1-Methylethylidene)-beta-D-fructopyranose 1-sulfamate;UNII-0KP2WFO28K;SCHEMBL6264898;DTXSID90442617;CKFVNUZYZFRVCR-JAKMQLQISA-N;J3.496.477G;J-001670;1-O-Sulfamoyl-2-O,3-O-isopropylidene-beta-D-fructopyranose;beta-D-Fructopyranose, 2,3-O-(1-methylethylidene)-, 1-sulfamate;.BETA.-D-FRUCTOPYRANOSE, 2,3-O-(1-METHYLETHYLIDENE)-, 1-SULFAMATE;[(3aS,6R,7R,7aS)-6,7-dihydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-3a-yl]methyl sulfamate;2,3-O-(1-Methylethylidene)-beta-D-fructopyranose 1-Sulfamate;5H-1,3-Dioxolo[4,5-b]pyran, beta-D-fructopyranose deriv.;Topiramate Impurity C

Chemical Property of 4,5-Desisopropylidene Topiramate

Chemical Property:

• Boiling Point: 503.3±60.0 °C(Predicted)
• PKA: 9.30±0.70(Predicted)
• PSA: 145.92000
• Density: 1.549±0.06 g/cm3(Predicted)
• LogP: -0.41260
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly, Sonicated), Water (Slightly, Heated)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 299.06748767
• Heavy Atom Count: 19
• Complexity: 446

Purity/Quality:

99.90% ^*data from raw suppliers

4,5-Desisopropylidene Topiramate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(COC2(O1)COS(=O)(=O)N)O)O)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H]([C@@H](CO[C@]2(O1)COS(=O)(=O)N)O)O)C
• Uses: A metabolite of Topiramate. A metabolite of Topiramate

Technology Process of 4,5-Desisopropylidene Topiramate

There total 2 articles about 4,5-Desisopropylidene Topiramate 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: 31.0%

topiramate (97240-79-4) → 2,3-O-(1-Methylethylidene)-β-D-fructopyranose 1-sulfamate (106881-41-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 45 ℃; for 3.5h;

DOI:10.1021/jm00388a023

Reference yield:

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose (20880-92-6) → 2,3-O-(1-Methylethylidene)-β-D-fructopyranose 1-sulfamate (106881-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH, 2.) sulfamoyl chloride / 1.) DMF, -4 deg C, 90 min, 2.) DMF, 0 deg C, 3.5 h

2: 31 percent / 3 N HCl / tetrahydrofuran / 3.5 h / 45 °C

With hydrogenchloride; sulphamoyl chloride; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jm00388a023

Reference yield: 77.0%

3-benzyloxypropanone (22539-93-1) + 2,3-O-(1-Methylethylidene)-β-D-fructopyranose 1-sulfamate (106881-41-8) → Sulfamic acid (3aS,5aR,8aR,8bS)-7-benzyloxymethyl-2,2,7-trimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester

Guidance literature:

With sulfuric acid; orthoformic acid triethyl ester; In tetrahydrofuran; ethanol; for 24h;

DOI:10.1016/S0008-6215(97)00214-0

upstream raw materials:

topiramate

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

Downstream raw materials:

topiramate

toluene-4-sulfonamide

Refernces