Synthetic method of beta-1,2,3,4,6-penta-acetyl-D-glucopyranose

A technology of glucopyranose and pentaacetyl, applied in the field of β-1, can solve the problem of low yield

Inactive Publication Date: 2009-11-11
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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  • Synthetic method of beta-1,2,3,4,6-penta-acetyl-D-glucopyranose
  • Synthetic method of beta-1,2,3,4,6-penta-acetyl-D-glucopyranose
  • Synthetic method of beta-1,2,3,4,6-penta-acetyl-D-glucopyranose

Examples

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Embodiment 1

[0022] Weigh 4.00 g of anhydrous sodium acetate and add it to a 100 mL round-bottomed three-neck flask, then add 25.00 mL of acetic anhydride, and stir. Heat to reflux with an oil bath, and after the solution becomes clear in 30 minutes, add a total of 5.00 g of anhydrous D-glucose within 30 minutes, then control the temperature of the oil bath at 130°C and continue heating for 2 hours to obtain a brown-yellow solution. Pour the reaction solution into a beaker filled with 250mL of ice water. A large amount of crystals precipitated in the lower part of the beaker. After stirring for 2 hours, let it stand, pour off the upper solution, wash the crystals twice with ice water, filter, collect the crystals, and dry to obtain a white crude product. 10.83 grams, the product was dissolved in absolute ethanol and refluxed for 0.5h, cooled, placed in ice water to precipitate crystals, filtered and dried. 8.10 g of the target product were obtained with a yield of 74.72% and a melting poin...

Embodiment 2

[0027] Weigh 4.00 g of anhydrous sodium acetate and add it to a 100 mL round-bottomed three-neck flask, then add 25.00 mL of acetic anhydride, and stir. Heat to reflux with an oil bath, and after the solution becomes clear for about 30 minutes, add a total of 5.00 g of anhydrous D-glucose within 30 minutes, then control the temperature at 140°C and continue heating for 4 hours to obtain a brown-yellow solution. Pour the reaction solution into a beaker containing 250 mL of crushed ice and ice water. A large number of crystals precipitated in the lower part of the beaker. After stirring for 4 hours, let it stand, pour off the upper liquid, wash the crystals twice with ice water, filter, collect the crystals, and dry them to white The crude product was 10.84 g. The product was dissolved in absolute ethanol and refluxed for 1 hour, cooled, placed in ice water to precipitate crystals, filtered and dried. Obtained 8.67 grams of dry white prismatic crystal sample. The yield is 80.00...

Embodiment 3

[0029] Weigh 4.00 g of anhydrous sodium acetate and add it to a 100 mL round-bottomed three-neck flask, then add 25.00 mL of acetic anhydride, and stir. Heat to reflux with an oil bath, after the solution becomes clear, add a total of 5.00 g of anhydrous D-glucose within 30 minutes, then control the temperature of the oil bath at 135°C and continue heating for 3 hours to obtain a brownish yellow solution. Pour the reaction solution into a beaker filled with 250mL of ice water. A large amount of crystals precipitated in the lower part of the beaker. After stirring for 3 hours, let it stand, pour off the upper solution, wash the crystals twice with ice water, filter, collect the crystals, and dry to obtain a white crude product. 10.83 grams, the product was dissolved in absolute ethanol and refluxed for 0.5h, cooled, placed in ice water to precipitate crystals, filtered and dried. 8.23 g of the target product were obtained with a yield of 75.93% and a melting point of 131.2-131....

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Abstract

The invention discloses a synthetic method of beta-1,2,3,4,6-penta-acetyl-D-glucopyranose, which is the improvement of the traditional technology, i.e., the heating reflux temperature in the anhydrous sodium acetate and acetic anhydride is improved; after the solution turns clear, anhydrous D-glucose is added; the reaction temperature is between 120 DEG C and 140 DEG C; the reaction time is 2-4h; the product is poured into ice water, stirred for 2-4h, and then washed and filtered to obtain white crude products; and the crude products are recrystallized by absolute ethyl alcohol, with the yield being improved to 74-80 percent. The obtained beta-1,2,3,4,6-penta-acetyl-D-glucopyranose has the melting point of 131.2-131.3 DEG C.

Description

technical field [0001] The invention relates to a synthesis method of β-1,2,3,4,6-pentaacetyl-D-glucopyranose, which belongs to the technical fields of medicine, biology and chemical industry. Background technique [0002] β-1,2,3,4,6-pentaacetyl-D-glucopyranose is a white crystalline powder, soluble in chloroform, insoluble in water. Melting point 131~132℃, [ α ] D 20 = + 4.5 ± 0.5 (C=5, CHCL 3 ), is an intermediate of medicine and biochemical industry, D-glucose exists in the form of cyclic hemiacetal in nature, and has two isomers, α and β. The hydroxyl group on glucose reacts with acetic anhydride to acetylate the five hydroxyl groups, correspondingly generating α and β pentaacetylglucopyranose. When anhydrous sodium acetate is used as a catalyst, the β-configuration pentaacetylglucopyranose is the main product, and ...

Claims

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Application Information

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IPC IPC(8): C07H13/06C07H1/00
Inventor 杨始刚嵇金丽顾静
Owner SHANGHAI INST OF TECH
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