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ChemicalBook--->CAS DataBase List--->1201913-82-7

1201913-82-7

1201913-82-7 Structure

1201913-82-7 Structure
IdentificationBack Directory
[Name]

TOFOGLIFLOZIN
[CAS]

1201913-82-7
[Synonyms]

CSG 452(hydrate)
Tofogliflozin(CSG452)
TOFOGLIFLOZIN USP/EP/BP
Tofogliflozin (hydrate)
Tofogliflozin anyhydrous
Tofogliflozin Monohydrate
Tofogliflozin hydrate (1:1)
Tofogliflozin Hydrate (JAN)
Tofogliflozin hydrate (1:1)-API
UNII-554245W62TTofogliflozin [INN]
Tofogliflozin hydrate (CSG-452 hydrate)
CSG452; CSG-452; TOFOGLIFLOZIN; CSG 452; UNII-554245W62TTOFOGLIFLOZIN [INN]; TOFOGLIFLOZIN ANYHYDROUS
(3S,3'R,4'S,5'S,6'R)-5-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)spiro[1H-2-benzofuran-3,2'-oxane]-3',4',5'-triol,hydrate
(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 hydrate (1:1)
[Molecular Formula]

C22H26O6.H2O
[MDL Number]

MFCD28385880
[MOL File]

1201913-82-7.mol
[Molecular Weight]

404.46
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH7.2)(1:20): 0.05 mg/ml
[form ]

A crystalline solid
[color ]

White to off-white
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Description]

Tofogliflozin hydrate, which is a sodium-glucose co-transporter 2 inhibitor, was approved in Japan for the treatment of type 2 diabetes at the same time as luseogliflozin hydrate (XIX). The drug was discovered by Chugai Pharmaceutical and jointly developed with Sanofi-Aventis and Kowa. Tofogliflozin hydrate reduces glucose levels by inhibiting the reuptake of glucose by selectively inhibiting SGLT2, and plays a key role in the reuptake of glucose in the proximal tubule of the kidneys.
[Synthesis]

Reduction of commercially available 2-bromoterephtalic acid (268) through the use of trimethoxyborane and borane- THF proceeded in 89% yield to afford diol 269. Subjection of this compound to 2-methoxypropene (270) under acidic conditions generated bis-acetonide 271. This bromide then underwent lithium¨Chalogen exchange followed by exposure to magnesium bromide and treatment with lactone 272 (which was prepared by persilylation of commercially available (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2Hpyran- 2-one (277). This mixture was worked up with aqueous ammonium chloride and upon treatment with p-TsOH in methanol resulted in spiroacetal 273. Next, global protection of all alcohol functionalities within 273 was affected by reaction with methylchloroformate and DMAP in acetonitrile. The benzyl carbonate within 274 was selectively exchanged via Suzuki coupling with 4-ethylphenylboronic acid (275) to afford methylene dibenzyl system 276. Subsequent treatment with aqueous sodium hydroxide in methanol followed by crystallization from 1:6 acetone and water furnished the desired product tofogliflozin hydrate (XXXIV) in 75% yield.

Synthesis_1201913-82-7

Spectrum DetailBack Directory
[Spectrum Detail]

TOFOGLIFLOZIN(1201913-82-7)1HNMR
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