1456719-03-1

Basic information

• Product Name: methyl [2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-6-deoxy-6-C-(ethylsulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-(2,3,6-tri-O-benzyl-α-D-glucopyranoside)
• Synonyms: methyl [2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-6-deoxy-6-C-(ethylsulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-(2,3,6-tri-O-benzyl-α-D-glucopyranoside)
• CAS NO: 1456719-03-1
• Molecular Weight: 1299.5
• Mol File: 1456719-03-1.mol

Chemical Properties

• CAS DataBase Reference: methyl [2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-6-deoxy-6-C-(ethylsulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-(2,3,6-tri-O-benzyl-α-D-glucopyranoside)(CAS DataBase Reference)
• NIST Chemistry Reference: methyl [2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-6-deoxy-6-C-(ethylsulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-(2,3,6-tri-O-benzyl-α-D-glucopyranoside)(1456719-03-1)
• EPA Substance Registry System: methyl [2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-6-deoxy-6-C-(ethylsulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-(2,3,6-tri-O-benzyl-α-D-glucopyranoside)(1456719-03-1)

Safety Data

• Hazardous Substances Data: 1456719-03-1(Hazardous Substances Data)

Upstream product

• 1456718-96-9 C₃₆H₄₂O₇S₂ 

Relevant articles and documents

A modular synthetic approach to isosteric sulfonic acid analogues of the anticoagulant pentasaccharide idraparinux

Heparin-based anticoagulants are drugs of choice in the therapy and prophylaxis of thromboembolic diseases. Idraparinux is a synthetic anticoagulant pentasaccharide based on the heparin antithrombin-binding domain. In the frame of our ongoing research aimed at the synthesis of sulfonic acid-containing heparinoid anticoagulants, we elaborated a modular pathway to obtain a series of idraparinux-analogue pentasaccharides bearing one or two primary sulfonic acid moieties. Five protected pentasaccharides with different C-sulfonation patterns were prepared by two subsequent glycosylation reactions, respectively, using two monosaccharide and four disaccharide building blocks. Transformation of the protected derivatives into the fully O-sulfated, O-methylated sulfonic acid end-products was also studied.

Synthesis of 6-sulfonatomethyl thioglycosides by nucleophilic substitution: Methods to prevent 1→6 anomeric group migration of thioglycoside 6-o-triflates

Introduction of a sulfonatomethyl moiety into the primary position of thioglycosides by nucleophilic displacement of the corresponding 6-O-triflate is described. The 1→6 migration of the anomeric group, which inevitably occurs through a bicyclic sulfonium ion intermediate, from conformationally flexible β-thioglycosides was prevented by using an α-thioglycoside or conformationally locked β-thioglycoside as the starting material. The thioglycoside 6-sulfonic acids showed excellent α-selectivity during synthesis of uronic acid containing heparinoid trisaccharides. Two routes to prepare C6-sulfonatomethyl thioglucosides by displacement of a 6-O-triflate moiety are reported. The undesired participation of the β-thio aglycon is prevented by changing the anomeric configuration or by locking the pyranose ring. The 6-sulfonatomethyl donors show excellent α-selectivities but significantly different reactivities during the synthesis of heparinoid trisaccharides. Copyright