| Identification | Back Directory | [Name]
(3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one | [CAS]
32384-65-9 | [Synonyms]
Canagliflozin Impurity 9
Dapagliflozin Impurity 12
2,3,4,6-Tetrakis-O-triMethylsilyl-D-gluconolactoe
2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
2,3,4,6-tetrakis-O-trimethylsilyl-D-glucono1,5 lactone
2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-1,5-lactone
D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, δ-lactone
D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, d-lactone
D-2,3,4,6-Tetrakis-O-(trimethylsilyl)-gluconic acid delta-lactone
(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-one
(3R,4S,5R,6R)-3,4,5-tris(triMethylsilyloxy)-6-((triMethylsilyloxy)Methyl)tetrahydro-2H-pyran-2-one
(3R,4S,5R,6R)-3,4,5-Tris[(trimethylsilyl)oxy]-6-[[(trimethylsilyl)oxy]methyl]tetrahydropyran-2-one
(3R,5R,6R)-3,4,5-Tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C18H42O6Si4 | [MDL Number]
MFCD22665922 | [MOL File]
32384-65-9.mol | [Molecular Weight]
466.864 |
| Chemical Properties | Back Directory | [Boiling point ]
417℃ | [density ]
0.97 | [Fp ]
171℃ | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Oil | [color ]
Colourless to Pale Yellow |
| Questions And Answer | Back Directory | [Description]
It is usually used as the intermediate and raw material in the chemistry synthesis and pharmaceutical industry. Especially, this chemical has been widely used in the design and synthesis of sodium-glucose transporter inhibitors.1 For example, this substance can be employed as raw material in the preparation of (1s)-1,5-anhydro-1-c-[4-chloro-3-[(4-ethoxylphenyl)methyl]phenyl]-D-glucitol, which is commonly known as Dapagliflozin that act as the sodium dependent glucose transporters for treating type 2 diabetes.2 Moreover, it can also function as the intermediate for synthesizing empagliflozin, which is a novel and selective sodium glucose co-transporter-2 inhibitor.3 In addition, canagliflozin, another sodium glucose co-transporter-2 inhibitor, can be obtained by utilizing this substance as the intermediate.4
| [Uses]
2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone is an antidiabetic agent and an intermediate of Dapagliflozin (D185370). 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone acts as a reagent in the synthesis of trans-cyclohexane-bearing C-glucose as sodium glucose co-transporter 2 inhibitors. | [Reference]
- Guo, C.; Hu, M.; DeOrazio, R. J.; Usyatinsky, A.; Fitzpatrick, K.; Zhang, Z. J.; Maeng, J. H.; Kitchen, D. B.; Tom, S.; Luche, M.; Khmelnitsky, Y.; Mhyre, A. J.; Guzzo, P. R.; Liu, S., The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties. Bioorg. Med. Chem. 2014, 22, 3414-3422.
- S Thirumalai Rajan; Eswaraiah, S., Process for the preparation of (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxylphenyl)methyl]phenyl]-D-glucitol and its solvate thereof. US Patent 2015, WO 2015/132803 A2.
- Hrapchak, M.; Latli, B.; Wang, X. J.; Lee, H.; Campbell, S.; Song, J. J.; Senanayake, C. H., Synthesis of empagliflozin, a novel and selective sodium-glucose co-transporter-2 inhibitor, labeled with carbon-14 and carbon-13. J. Label. Compd. Radiopharm. 2014, 57, 687-694.
- Nomura, S.; Sakamaki, S.; Hongu, M.; Kawanishi, E.; Koga, Y.; Sakamoto, T.; Yamamoto, Y.; Ueta, K.; Kimata, H.; Nakayama, K.; Tsuda-Tsukimoto, M., Discovery of Canagliflozin, a Novel C-Glucoside with Thiophene Ring, as Sodium-Dependent Glucose Cotransporter 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus. J. Med. Chem. 2010, 53, 6355-6360.
|
|
|