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Preparation method for (1S)-1,6-dideoxy-1-[4-hydroxy-3-(trans-4-substituted cyclohexyl) methyl phenyl]-D-glucopyranose compound

A compound and deacetylation technology, applied in the field of medicine, can solve the problems of relatively large yield fluctuation, low overall route yield, poor route reproducibility, etc.

Inactive Publication Date: 2014-01-15
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] There are still many shortcomings in the above-mentioned route for preparing SGLT2 inhibitor I: the productive rate converted from P3 to P4 is low, resulting in a low overall route yield for the final preparation of I, and the reproducibility of this route is not good, and the productive rate is between The fluctuation between batches is relatively large

Method used

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  • Preparation method for (1S)-1,6-dideoxy-1-[4-hydroxy-3-(trans-4-substituted cyclohexyl) methyl phenyl]-D-glucopyranose compound
  • Preparation method for (1S)-1,6-dideoxy-1-[4-hydroxy-3-(trans-4-substituted cyclohexyl) methyl phenyl]-D-glucopyranose compound
  • Preparation method for (1S)-1,6-dideoxy-1-[4-hydroxy-3-(trans-4-substituted cyclohexyl) methyl phenyl]-D-glucopyranose compound

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Embodiment 1

[0047] [1]

[0048]

[0049] Add 32.52g (0.1mol) compound XIV-1, 20.52g (0.12mol) benzyl bromide, 27.64g (0.2mol) solid K in a dry 500mL round bottom flask 2 CO 3 , 5.00 g of solid KI and 200 mL of dry DMF, the resulting mixture was stirred at room temperature overnight, TLC showed that the reaction was complete.

[0050] The reaction mixture was washed with 500 mL CH 2 Cl 2 Dilute, stir for 1 minute, and filter with suction to remove solids. The filtrate was washed with saturated brine, anhydrous Na 2 SO 4 After drying, the desiccant was removed by suction filtration, and the solvent was evaporated in a rotary evaporator to obtain a colorless oil, which was purified by column chromatography to obtain the pure product XIII-1, 37.80 g, with a yield of 91%. Colorless crystals, melting point 63-65°C, 1 H NMR (DMSO-d 6 ,400MHz),δ7.67(dd,1H,J=2.4Hzand8.8Hz),7.53(d,1H,J=2.8Hz),7.35-7.49(m,5H),7.25(d,1H,J=8.8 Hz),5.19(s,2H),3.01-3.08(m,1H),1.71-1.74(m,2H),1.59-1.63(m,2H)...

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Abstract

The invention belongs to the technical field of medicine, and particularly relates to a preparation method for a (1S)-1,6-dideoxy-1-[4-hydroxy-3-(trans-4-substituted cyclohexyl) methyl phenyl]-D-glucopyranose compound, wherein R is equal to H, Me, Et and n-Pr.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation method of C-glucoside containing a saturated cyclohexane structure. Background technique [0002] There are currently about 170 million diabetics in the world, and the vast majority of them are type II (ie, non-insulin-dependent) diabetics. The antidiabetic drugs currently in clinical use mainly include metformin, sulfonylureas, insulin, thiazolidinediones, α-glucosidase inhibitors and dipeptidyl peptidase-IV inhibitors. It has a good therapeutic effect, but there are safety problems in long-term treatment, such as: liver toxicity, some drugs still have weight gain and many other problems. [0003] Sodium-glucose cotransporter type 2 (SGLT2) is a new target for the treatment of diabetes discovered in recent years. SGLT2 is mainly distributed in the proximal tubule of the kidney. Its function is to absorb glucose in urine and return it to the blood. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10
CPCC07D309/10
Inventor 赵桂龙汤立达邵华魏群超王玉丽徐为人邹美香吴疆
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH