106881-35-0

Basic information

• Product Name: 2,3:4,5 Bis-O-(1-Methyl ethylidene)-Fructopyranose azido sulphate
• Synonyms: 2,3:4,5 Bis-O-(1-Methyl ethylidene)-Fructopyranose azido sulphate;2,3:4,5-Bis-O-(1-(1-MethylEthylidene)-B-;2,3:4,5-Bis-O-(1-Methylethylidene)-B-fructopyranoseazidosulfate;TopiraMate Azidosulfate;2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose azide sulphate;2,3:4,5-Bis-O-(1-Methylethylidene)-β-D-fructopyranose Azidosulfate;2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose 1-azidosulfate
• CAS NO: 106881-35-0
• Molecular Formula: C₁₂H₁₉N₃O₈S
• Molecular Weight: 365.35956
• Product Categories: Carbohydrates & Derivatives;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 106881-35-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3:4,5 Bis-O-(1-Methyl ethylidene)-Fructopyranose azido sulphate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3:4,5 Bis-O-(1-Methyl ethylidene)-Fructopyranose azido sulphate(106881-35-0)
• EPA Substance Registry System: 2,3:4,5 Bis-O-(1-Methyl ethylidene)-Fructopyranose azido sulphate(106881-35-0)

Safety Data

• Hazardous Substances Data: 106881-35-0(Hazardous Substances Data)

Usage

Uses

Topiramate (T540250) impurity.

Upstream product

• 97240-79-4 topiramate 
• 150609-95-3 2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester 
• 20880-92-6 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose 

Downstream Products

• 97240-79-4 topiramate 

Relevant articles and documents

Modular click chemistry libraries for functional screens using a diazotizing reagent

Click chemistry is a concept in which modular synthesis is used to rapidly find new molecules with desirable properties1. Copper(i)-catalysed azide–alkyne cycloaddition (CuAAC) triazole annulation and sulfur(vi) fluoride exchange (SuFEx) catalysis are widely regarded as click reactions2–4, providing rapid access to their products in yields approaching 100% while being largely orthogonal to other reactions. However, in the case of CuAAC reactions, the availability of azide reagents is limited owing to their potential toxicity and the risk of explosion involved in their preparation. Here we report another reaction to add to the click reaction family: the formation of azides from primary amines, one of the most abundant functional groups5. The reaction uses just one equivalent of a simple diazotizing species, fluorosulfuryl azide6–11 (FSO2N3), and enables the preparation of over 1,200 azides on 96-well plates in a safe and practical manner. This reliable transformation is a powerful tool for the CuAAC triazole annulation, the most widely used click reaction at present. This method greatly expands the number of accessible azides and 1,2,3-triazoles and, given the ubiquity of the CuAAC reaction, it should find application in organic synthesis, medicinal chemistry, chemical biology and materials science.

Anticonvulsant O-Alkyl Sulfamates. 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose Sulfamate and Related Compounds.

Novel sugar sulfamate 1 (McN-4853, topiramate) has been found to exhibit potent anticonvulsant activity analogous to that of phenytoin.In the maximal electroshock seizure test, orally at 2 h in mice, 1 had an ED50 of 39 mg/kg.Orally, 1 had a duration of action in excess of 8 h.Other aspects of the pharmacology of 1, as well as neurochemistry and carbonic anhydrase inhibition, are discussed.The conformational behavior of 1 in solution and in the solid state are discussed.A series of analogues of 1 were synthesized and examined for anticonvulsant properties.