1283129-20-3

Basic information

• Product Name: 2,3,4,6-tetra-O-pivaloyl 1-(2-anisyl)-1-deoxy-β-D-glucopyranose
• Synonyms: 2,3,4,6-tetra-O-pivaloyl 1-(2-anisyl)-1-deoxy-β-D-glucopyranose
• CAS NO: 1283129-20-3
• Molecular Weight: 606.754
• Mol File: 1283129-20-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-pivaloyl 1-(2-anisyl)-1-deoxy-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-pivaloyl 1-(2-anisyl)-1-deoxy-β-D-glucopyranose(1283129-20-3)
• EPA Substance Registry System: 2,3,4,6-tetra-O-pivaloyl 1-(2-anisyl)-1-deoxy-β-D-glucopyranose(1283129-20-3)

Safety Data

• Hazardous Substances Data: 1283129-20-3(Hazardous Substances Data)

Upstream product

• 82303-13-7 (4-methoxyphenyl)zinc(II) bromide 
• 97302-05-1 di-4-methoxyphenylzinc 
• 181705-90-8 (3-methoxyphenyl)zinc(II) bromide 
• 684215-27-8 bis-(3-methoxyphenyl)zinc 
• 958300-05-5 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosylbromide 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1218904-46-1 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl iodide 
• 81058-27-7 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide 

Relevant articles and documents

Pivaloyl-protected glucosyl iodide as a glucosyl donor for the preparation of β-C-glucosides

A method for the selective synthesis of β-C-glucosides using α-D-tetra-O-pivaloylglucosyl iodide as a glucosyl donor is reported. Its diastereoselectivity differs from that of the respective acetyl-protected glucosyl bromide, as it reported in the literature under similar reaction conditions. The concentration of the catalyst, the solvent and the type of additive used are crucial factors that determine the reaction selectivity. This method has been applied in a short synthesis of dapagliflozin. The stability of α-D-tetra-O-pivaloylglucosyl iodide in CDCl3 and THF at reflux was also studied. All side products in the coupling and decomposition reactions were isolated and characterized, and possible pathways for their formation are proposed.

Exploiting Synergistic Effects in Organozinc Chemistry for Direct Stereoselective C-Glycosylation Reactions at Room Temperature

Pairing a range of bis(aryl) zinc reagents ZnAr2 with the stronger Lewis acidic [(ZnArF2)] (ArF=C6F5), enables highly stereoselective cross-coupling between glycosyl bromides and ZnAr2 without the use of a transition metal. Reactions occur at room temperature with excellent levels of stereoselectivity, where ZnArF2 acts as a non-coupling partner although its presence is crucial for the execution of the C(sp2)–C(sp3) bond formation process. Mechanistic studies have uncovered a unique synergistic partnership between the two zinc reagents, which circumvents the need for transition-metal catalysis or forcing reaction conditions. Key to the success of the coupling is the avoidance of solvents that act as Lewis bases versus diarylzinc compounds (e.g. THF).

PROCESS FOR THE PREPARATION OF COMPOUNDS USEFUL AS INHIBITORS OF SGLT2

The present invention is directed to a novel process for the preparation of compounds having inhibitory activity against sodium-dependent glucose transporter (SGLT) being present in the intestine or kidney.