903565-83-3

Basic information

• Product Name: Tofogliflozin
• Synonyms: Tofogliflozin;(1S,3'R,4'S,5'S,6'R)-6-[(4-Ethylphenyl)Methyl]-3',4',5',6'-tetrahydro-6'-(hydroxyMethyl)spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triol;CSG 452;((1S,3'R,4'S,5'S,6'R)-6-(4-ethylbenzyl)-3',4',5'-trihydroxy-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-6'-yl)methyl propionate;(1S,3'R,4'S,5'S,6'R)-6'-(hydroxymethyl)-6-(methoxymethyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol
• CAS NO: 903565-83-3
• Molecular Formula: C22H26O6
• Molecular Weight: 386.43824
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 903565-83-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 607.5±55.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3 (20 ºC 760 Torr), Calc.*
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.06±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Tofogliflozin(CAS DataBase Reference)
• NIST Chemistry Reference: Tofogliflozin(903565-83-3)
• EPA Substance Registry System: Tofogliflozin(903565-83-3)

Safety Data

• Hazardous Substances Data: 903565-83-3(Hazardous Substances Data)

Usage

Description

Tofogliflozin is a novel, potent, and highly selective SGLT2 inhibitor that has been shown to improve glycemic control in diabetic mice and rats.

Uses

Used in Pharmaceutical Industry:
Tofogliflozin is used as an antidiabetic medication for improving glycemic control in diabetic patients. It works by inhibiting the SGLT2 protein, which helps to reduce glucose reabsorption in the kidneys and promote its excretion through urine, leading to a decrease in blood glucose levels.

Upstream product

• 1201913-74-7 (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate) 
• 90-80-2 D-Glucono-1,5-lactone 
• 18643-86-2 dimethyl 2-bromoterephthalate 
• 586-35-6 2-bromo-1,4-benzenedicarboxylic acid 
• 903566-65-4 (1S,3′R,4′S,5′S,6′R)-3′,4′,5′,6′-tetrahydro-6,6′-bis(hydroxymethyl)spiro[2-benzofuran-1(3H),2-[2H]pyran]-3′,4′,5′-triol 
• 1019209-73-4 2-bromo-1,4-bis(((2-methoxypropan-2-yl)oxy)methyl)benzene 
• 89980-92-7 (2-bromo-1,4-phenylene) dimethyl carbinol 
• 1426923-29-6 (3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-5-chloro-6-(4-ethylbenzyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran] 
• 1426923-28-5 [4-(4-ethylbenzyl)-2-bromo-5-chlorobenzyloxy]trimethylsilane 
• 1313513-41-5 methyl 2-bromo-4-(bromomethyl)-5-chlorobenzoate 
• 1426923-27-4 C₈H₆BrClO₂ 

Relevant articles and documents

Synthesis of Tofogliflozin as an SGLT2 Inhibitor via Construction of Dihydroisobenzofuran by Intramolecular [4 + 2] Cycloaddition

The synthesis of tofogliflozin (1), a sodium glucose cotransporter 2 (SGLT2) inhibitor, was achieved through the key steps of intramolecular [4 + 2] cycloaddition of dienone-yne intermediate, aerobic aromatization, and anomeric equilibration, thus enablin

Preparation method of Tofogliflozin monohydrate

The invention relates to a preparation method of Tofogliflozin monohydrate. In the route, p-Hydroxybenzoic acid used as a starting material is subjected to acylation, iodination, Friedel-Crafts and reduction reaction to obtain an iodinated diphenylmethane framework; by means of the characteristic that an iodinated substance is reactive, the splicing the diphenylmethane framework and a saccharide ring is realized under mild conditions through the effect of isopropyl magnesium chloride lithium chloride; and the eleven-step total yield is 22%. The route is high in yield, favorable in selectivity, low in production cost and mild in reaction conditions, does not use flammable, explosive or high-toxicity reagent, obtains products and intermediate compounds which are easy to purify, and is suitable for industrial production.

Method for preparing derivatives of spiroketal

Provided is a process for the preparation of a spiroketal derivative via a compound represented by general formula (II) [wherein each variable group and each variable number are as defined in the description].