D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, d-lactone
2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
CAS: 32384-65-9
Molecular Formula: C18H42O6Si4
D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, d-lactone - Names and Identifiers
D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, d-lactone - Physico-chemical Properties
| Molecular Formula | C18H42O6Si4 |
| Molar Mass | 466.87 |
| Density | 0.97 |
| Boling Point | 417℃ |
| Flash Point | 171℃ |
| Solubility | Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| Appearance | Oil |
| Color | Colourless to Pale Yellow |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
D-Gluconic acid, 2,3,4,6-tetrakis-O-(triMethylsilyl)-, d-lactone - Reference Information
| overview | the chemical name of canagliflozin (canagliflozin,1) is (1S) -1,5-dehydrated-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl] methyl]-4-methylphenyl]-D-glucitol, developed by Tanabe Mitsubishi and Johnson & Johnson, it was approved by FDA on March 29, 2013. It is the first sodium glucose cotransporter 2 ( SGLT2) inhibitor approved by FDA. The drug was approved by the European Commission (EC) on November 25, 2013 for the treatment of type 2 diabetes in adults. By inhibiting SGLT2, canagliflozin makes the glucose in the renal tubules unable to be smoothly reabsorbed into the blood and excreted in the urine, thereby reducing the blood sugar concentration. |
| Use | 2,3,4,6-tetra-O-trimethylsilyl-D-glucosyl -1,5-Lactone is an antidiabetic drug and an intermediate of dapaglifloin. 2,3,4,6-Tetra-O-trimethylsilyl-D-glucosyl-1, 5-lactone as a reagent for the synthesis of trans-cyclohexane-containing C- glucose as a sodium glucose cotransporter 2 inhibitor. |
| Clinical application | The drug of canaglifloin can reduce the fasting blood glucose, glycosylated hemoglobin and body mass of patients, and the use of this drug can significantly reduce the risk of hypoglycemia during treatment. Although the symptoms of reproductive system infection, polyuria, frequent urination and other symptoms are still relatively high compared to the control group, but it still has a very obvious effect on lowering blood sugar. It has very important clinical significance and value in the treatment of clinical type 2 diabetes. |
| Preparation | Using gluconolactone (2) as the starting material, under the catalysis of N-methylmorpholine (NMM), it reacts with trimethylchlorosilane in tetrahydrofuran to obtain the key intermediate 2,3,4, 6-tetra-O-trimethylsilyl-D-gluconolactone (3); 2-[(5-bromo-2-methylphenyl) methyl]-5-(4-fluorophenyl) thiophene (4) is treated with n-butyl lithium at -8 ℃ and then condensed with compound 3 to obtain Compound 5 (The condensation reaction temperature is controlled at -7~0 ℃); after the reaction is over, the reaction temperature is maintained, the reaction solution is not treated, and methanesulfonic acid and methanol are added dropwise, slowly raised to room temperature and stirred to obtain deprotected compound 6 (the yield of this reaction is 91. 3%, and the purity of the product is 88.5%); Compound 6 is reduced by triethylsilane (Et3SiH) or triisopropylsilane (TIPS) and boron trifluoride ether to obtain canagliflozin (1), the yield of this step is 56. 7%, and the purity of the product is 99. 5%. |
Last Update：2024-04-09 21:11:58
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