- Preparing methods of ipragliflozin intermediates
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The invention discloses preparing methods of ipragliflozin intermediates. The methods includes preparing methods for 2-(3-benzo[B]thien-2-ylmethyl-4-fluorophenyl)-3,4,5-tris(trimethylsiloxy)-6-trimethylsiloxymethyl-tetrahydro-pyran-2-ol (a compound 3) and (1S)-2,3,4,6-tetraacetoxy-1,5-anhydro-1-[3-(1-benzothiophen-2-yl-methyl)-4-fluorophenyl]-D-glucitol (a compound 6). Under the premise of controlling the temperature of a reaction solution to be not higher than -60 DEG C, n-butyllithium should be added dropwise as soon as possible, and the higher the adding speed of the n-butyllithium is, theless F-ortho-position substituted side products of the compound 3 are, thus ensuring purity of the compound 3 and directly influencing the yield of the compound 6 finally prepared. Through scale-up, the methods are free of scale-up effects, and are suitable for industrial production.
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- Synthetic method of Ipragliflozin
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The invention provides a synthetic method of Ipragliflozin. The synthetic method comprises the following steps: exchanging a prepared compound organic metallic reagent and 2-(5-bromo-2-benzyl) benzothiophene halogen to obtain an arene metal compound intermediate; enabling coupling reaction between the arene metal compound intermediate and glucolactone; conducting dehydroxylation protection to obtain 1-C-[3-(benzo[B]thien-2-ylmethyl)-4-fluorophenyl]-ALPHA-D-pyran glucitol; reducing 1-C-[3-(benzo[B]thien-2-ylmethyl)-4-fluorophenyl]-ALPHA-D-pyran glucitol to obtain crude Ipragliflozin; conducting acylation, recrystallization and deacylation reaction on crude Ipragliflozin to obtain pure Ipragliflozin. As the compound organic metallic reagent is adopted, the reaction temperature is improved, the cost is lowered, and the synthetic method is suitable for industrial production; as water solution dehydroxylation protection of acid is adopted, the crude product is a solid but not an oily substance; the disposal is convenient and the reaction time is shortened.
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- METHOD FOR PRODUCING C-GLYCOSIDE DERIVATIVE AND SYNTHETIC INTERMEDIATE THEREOF
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The present invention provides a method for producing a C-glycoside derivative, which can produce the C-glycoside derivative at a high yield and at a low cost, which conforms to environmental protection, and which is applicable industrially. The C-glycoside derivative is useful for treating and preventing diabetes such as insulin-dependent diabetes (type 1 diabetes), non-insulin-dependent diabetes (type 2 diabetes) and the like and various diabetes-related diseases including insulin-resistant diseases and obesity.
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Page/Page column 14-15
(2009/10/06)
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