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2-deoxy-n-phenyl pentosamine preparation method

A technology of phenylpentosamine and glucose, which is applied in the field of preparation of 2-deoxy-N-phenylpentosamine, can solve the problems of high preparation cost, high requirements for preparation conditions, low yield, etc., and achieve the preparation method Simple, simple reaction conditions, and easy industrial production

Inactive Publication Date: 2015-08-12
SUZHOU WISMED PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 2-deoxy-N-phenylpentosamine is an important intermediate for the synthesis of nucleoside compounds. There are many synthetic methods for 2-deoxy-N-phenylpentosamine, but often due to the relatively Complicated and high requirements for preparation conditions, low yield, so its preparation cost is also high, and the prepared 2-deoxy-N-phenylpentosamine is often pure, which brings difficulties to further reaction and separation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Add 20kg of isobutylene to 100kg of D-glucose, add 0.1kg of aluminum chloride and 0.2kg of hydrochloric acid under nitrogen at 0°C, and stir at 65°C for 2 hours to obtain 1,2,4,6 bicyclohexylidene -D-glucose;

[0025] (2) Add 2 kg of methanesulfonyl chloride, slowly add 0.02 kg of triethylamine at 0°C, and react at 90°C for 5 hours to obtain 1,2,5,6-bis-oxygen-isopropylidene-α- D-glucose;

[0026] (3) adding hydrochloric acid to adjust the pH value to 4.5, and stirring at 70° C. for 1 hour to obtain 3-oxo-p-toluenesulfonyl-D-glucose;

[0027] (4) Add 0.02 kg of sodium hydroxide, and heat in methanol solution at 75° C. for 1 hour to obtain 2-deoxy-D-ribose;

[0028] (5) Add 1.5 kg of aniline and 0.02 kg of sodium bicarbonate, reflux in methanol solution for two hours, add 0.1 kg of sodium borohydride and stir to obtain 2-deoxy-N-phenylpentosamine with a yield of 68.5%, The melting point is 166-167°C.

Embodiment 2

[0030] (1) Add 50 kg of isobutylene to 100 kg of D-glucose, add 0.3 kg of aluminum chloride and 0.8 kg of hydrochloric acid under nitrogen at 5°C, and stir at 55°C for 3 hours to obtain 1,2,4,6 bicyclohexylidene -D-glucose;

[0031] (2) Add 5 kg of methanesulfonyl chloride, slowly add 0.05 kg of triethylamine at 5°C, and react at 80°C for 6 hours to obtain 1,2,5,6-bis-oxygen-isopropylidene-α- D-glucose;

[0032] (3) adding hydrochloric acid to adjust the pH value to 6, stirring at 55°C for 2 hours to obtain 3-oxo-p-toluenesulfonyl-D-glucose;

[0033] (4) Add 0.08 kg of sodium hydroxide, and heat in methanol solution at 80° C. for 2 hours to obtain 2-deoxy-D-ribose;

[0034] (5) Add 3 kg of aniline and 0.05 kg of sodium bicarbonate, reflux in methanol solution for two hours, add 0.3 kg of sodium borohydride and stir to obtain 2-deoxy-N-phenylpentosamine with a yield of 63.1%, melting point It is 166-167°C.

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Abstract

The invention discloses a 2-deoxy-N-phenyl pentosamine preparation method. The 2-deoxy-N-phenyl pentosamine preparation method includes the steps: (1) adding isobutene into D-glucose, adding aluminum chloride and hydrochloric acid under a nitrogen condition at the temperature of 0-5 DEG C, and stirring for 2-3 hours at the temperature of 55-65 DEG C; (2) adding methanesulfonyl chloride, slowly adding triethylamine at the temperature of 0-5 DEG C, and reacting for 5-6h at the temperature of 80-90 DEG C; (3) adding hydrochloric acid to adjusting the pH value to 4.5-6, and stirring for 1-2h at the temperature of 55-70 DEG C; (4) adding sodium hydroxide, and heating in methanol solution for 1-2h at the temperature of 75-80 DEG C; (5) adding aniline and sodium bicarbonate, back flowing for two hours in the methanol solution, adding sodium borohydride and stirring to obtain 2-deoxy-N-phenyl pentosamine.

Description

technical field [0001] The invention belongs to the field of sugar amine preparation, in particular to a preparation method of 2-deoxy-N-phenylpentosamine. Background technique [0002] The -OH on the highest numbered chiral C atom of D-glucose is on the right, also known as dextrose, which can be obtained by hydrolysis of starch and often exists in free form in grapes, honey, sweet fruits, animal blood, spinal fluid and lymph fluid Among them, it also exists widely in nature as a component of polysaccharides and in the form of glycosides. [0003] 2-deoxy-N-phenylpentosamine is an important intermediate for the synthesis of nucleoside compounds. There are many synthetic methods for 2-deoxy-N-phenylpentosamine, but often due to the relatively Complexity and high requirements for preparation conditions, low yield, and thus high preparation costs, and the prepared 2-deoxy-N-phenylpentosamine is often pure, which brings difficulties to further reaction and separation. Conten...

Claims

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Application Information

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IPC IPC(8): C07H5/06C07H1/00
Inventor 王芃
Owner SUZHOU WISMED PHARMA CO LTD
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