Tofogliflozin

Base Information

• Chemical Name: Tofogliflozin
• CAS No.: 903565-83-3
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445
• Mol file: 903565-83-3.mol

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

Chemical Property of Tofogliflozin

Chemical Property:

• Boiling Point: 607.5±55.0 °C(Predicted)
• PKA: 13.06±0.70(Predicted)
• PSA: 99.38000
• Density: 1.38±0.1 g/cm3 (20 ºC 760 Torr), Calc.*
• LogP: 0.99660
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

Tofogliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A novel, potent, and highly selective SGLT2 inhibitor that has been shown to improve glycemic control in diabetic mice and rats.

Technology Process of Tofogliflozin

There total 51 articles about Tofogliflozin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(1S,3′R,4′R,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran] (1201913-68-9) → (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 (903565-83-3)

Guidance literature:

With sodium hydroxide; In methanol; 1,2-dimethoxyethane; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.5b02734

Reference yield: 99.0%

1,1-anhydro-1-C-[5-(4-ethylphenyl)methyl-2-(hydroxymethyl)phenyl]-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose → (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 (903565-83-3)

Guidance literature:

With hydrogen; 10percent palladium catalyst; In methanol; ethyl acetate; at 20 ℃; for 5h;

Reference yield: 79.0%

(1S,3'R,4'S,5'S,6'R)-6-(4-ethylphenyl)-6'-(methoxymethyloxymethyl)-3',4',5',6'-tetrahydro-3',4',5'-trimethoxycarbonyloxy-3H-spiro[isobenzofuran-1,2'-pyran] → (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 (903565-83-3)

Guidance literature:

With sodium hydroxide; In 1,2-dimethoxyethane; water; at 20 ℃; for 3h;

upstream raw materials:

D-Glucono-1,5-lactone

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

2,4-dibromo-1-(1-methoxy-1-methylethoxymethyl)benzene

(2,4-dibromophenyl)methanol

Refernces

• 1、 Murakata, Masatoshi,Ikeda, Takuma,Kimura, Nobuaki,Kawase, Akira,Nagase, Masahiro,Kimura, Masahiro,Maeda, Kenji,Honma, Akie,Shimizu, Hitoshi. "The regioselective bromine-lithium exchange reaction of alkoxymethyldibromobenzene: A new strategy for the synthesis of tofogliflozin as a SGLT2 inhibitor for the treatment of diabetes". . p. 655 - 660. Retrieved 2017/01/16.
• 2、 -. "Method for preparing derivatives of spiroketal". . . Retrieved 2016/10/07.