Method for synthesizing 2-deoxy-L-ribose

A ribose and reaction technology, applied in the field of 2-deoxy-L-ribose synthesis, can solve the problems of cumbersome steps, time-consuming and low yield, and achieve the effect of easy post-processing, high yield and simple reaction operation

Inactive Publication Date: 2009-04-15
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by this invention is in order to overcome the method steps of the prior art by 1-methyl-3,4-O-isopropyl-2-deoxy-β-L-arabinose

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1-Methyl-3,4-O-isopropyl-2-deoxy-β-L-arabinose (22g) was dissolved in 200ml of saturated aqueous benzoic acid (0.34wt%), and the reaction solution was refluxed (110°C ) under stirring for 1 hour (TLC detection control time), the reaction solution was cooled to room temperature, CHCl 3 (50ml) was extracted and washed 3 times, the water phase was distilled under reduced pressure to 1 / 2 of the original volume, 0.22g of activated carbon was added and stirred at room temperature for 1 hour, then the water phase was filtered and evaporated to dryness to obtain a light yellow syrup (14.89g, 95 %), purity: 99.0%. [α] D 20 +50° (c=1.0, H 2 O) [lit. [7a] [α] D 20 +60°(c=1.06, H 2 O)]; 1 H NMR (400MHz, DMSO-d 6 ): δ1.47 and 1.78 (m, 2H, H 2 , H 2′ ), 3.46-3.53 (m, 2H, H 5 , H 5′ ), 3.63 (m, 1H, H 4 ), 3.83 (m, 1H, H 3 ), 4.32-4.35 (m, 2H, -OH 3 ,-OH 5 ), 4.97 (m, 1H, H 1 ), 6.00 (d, 1H, -OH 1 ); MS: m / z 157.07 [M + +Na], 173.04[M + +K].

Embodiment 2

[0024] 1-Methyl-3,4-O-isopropyl-2-deoxy-β-L-arabinose (22g) was dissolved in 200ml of 0.01wt% benzoic acid aqueous solution, and the reaction solution was stirred at 100°C for 1 hour (TLC detection control time), the reaction solution is cooled to room temperature, CHCl 3 (50ml) was extracted and washed twice, the water phase was distilled under reduced pressure to 0.25 of the original volume, 1.1 g of activated carbon was added and stirred at room temperature for 0.5 hours, then the water phase was filtered and evaporated to dryness to obtain a light yellow syrup (7.84 g, 50%) , with a purity of 90.0%. Identification result is the same as embodiment 1.

Embodiment 3

[0026] 1-Methyl-3,4-O-isopropyl-2-deoxy-β-L-arabinose (22g) was dissolved in 200ml of 0.1wt% benzoic acid aqueous solution, and the reaction solution was stirred at 80°C for 2 hours (TLC detection control time), the reaction solution is cooled to room temperature, CHCl 3 (50ml) was extracted and washed 3 times, the water phase was distilled under reduced pressure to 1 / 3 of the original volume, 0.8g of activated carbon was added and stirred at room temperature for 10 minutes, then the water phase was filtered and evaporated to dryness to obtain a light yellow syrup (11.76g, 75 %), purity: 99.0%. Identification result is the same as embodiment 1.

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Abstract

The invention discloses a method for synthesizing 2-deoxidization-L-ribose, and the method is characterized in that 1-methyl-3, 4-O-isopropyl-2-deoxidization-beta-L-gum sugar reacts in water solution of organic acid with acidity more than that of acetic acid. The final product can be obtained in one step of reaction by the method, and the method has the advantages of simple reaction operation, easy post processing, without the need of column chromatography, high yield and purity, thus being suitable for industrialization production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 2-deoxy-L-ribose. Background technique [0002] Documents (Synthesis and properties of mirror-image DNA; Urata, H., Ogura, E., Shinohara, K., Ueda, Y., Akagi, M.J.; Nucleic Acids Res. 1992, 20, 3325-3332) disclose The method for synthesizing 2-deoxy-L-ribose from raw material 1-methyl-3,4-O-isopropyl-2-deoxy-β-L-arabinose, which includes two-step reactions: (1) converting 1-methyl The base-3,4-O-isopropylidene-2-deoxy-β-L-arabinose reacted in 80% acetic acid solution for 15 hours to hydrolyze the isopropylidene protecting group, and obtained 1-methyl- 2-deoxy-L-pentopyranose; (2) After that, react 1-methyl-2-deoxy-L-pentopyranose in 0.8M HCl solution for 40 hours to hydrolyze the terminal methyl protecting group , the product 2-deoxy-L-ribose was obtained by Dowex 1-X2 basic resin. The operation process of this method is cumbersome, the yield is low, ...

Claims

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Application Information

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IPC IPC(8): C07H3/08
Inventor 明逊陈莉莉岑均达
Owner SHANGHAI INST OF PHARMA IND
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