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Method for synthesizing 1,2,3-O-tri-acetyl-5-deoxidation-D-ribose

A synthetic method and acetyl group technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve problems such as difficult crystallization, high cost, and high bond breaking temperature

Inactive Publication Date: 2008-05-21
HEFEI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the iodine / imidazole / triphenylphosphine system is used to replace the 5-position hydroxyl of inosine ribose, the cost is high, and the acetylation bond breaking temperature is high, there are many by-products, and it is difficult to crystallize

Method used

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  • Method for synthesizing 1,2,3-O-tri-acetyl-5-deoxidation-D-ribose

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Experimental program
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Embodiment Construction

[0019] (1) Synthesis of 2,3-O-isopropylidene-5-O-tosyl-D-furanoside (I)

[0020] Add 150 g of ribose into a three-necked flask, add 5 times the amount of methanol and acetone respectively and stir at 40 ° C, adjust the pH to 3 to 4 with concentrated sulfuric acid, stir until clear, and detect the degree of reaction by TLC (ethyl acetate:petroleum ether 60～90℃ =9:1), after the reaction is over, add pyridine or triethylamine to adjust the pH to 6-7, stir for 20min, filter with suction, reclaim the solvent under reduced pressure to dryness, directly add 210g of toluenesulfonyl chloride for esterification in batches, and when the reaction ends, The reaction solution was poured into ice water to cool and crystallized to obtain 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-D-furanoside, which was refined to obtain 289 g of white solid, mp 78-80°C, yield Rate 80%.

[0021] (2) Synthesis of 2,3-O-isopropylidene-5-iodo-5-deoxy-D-furanoside (II)

[0022] 289g of intermediate (I) was heat...

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Abstract

The invention discloses a synthesis method of 1, 2, 3-O-tri-acetyl-5-deoxy-D-ribose. D-ribose is used as a starting raw material for methyl glycosidation, propylidene and esterification (one-pot method) to obtain 2, 3-O-isopropylidene-5-O-p-tolylsulfonyl-D-furan methyl glycoside which is reduced, hydrolyzed and acetylated to obtain the target product 1, 2, 3-O-tri-acetyl-5-deoxy-D-ribose. The synthesis technology is simple and convenient; the reaction condition is gentle; the raw material is cheap and can be obtained easily; the cost is low; the invention causes no environmental pollution; the total yield is high, and the total yield of the four steps is 37.8 percent; the invention is quite applicable to the industrial production; the product melting point is 62 DEG C to 64 DEG C.

Description

technical field [0001] The present invention relates to a synthesis method of a pharmaceutical intermediate, in particular to a broad-spectrum, high-efficiency, low-toxic antitumor drug, such as 5'-deoxy-5-fluorouridine, 5'-deoxy-5-fluorocytidine, 5′-deoxythymidine, 5′-deoxyadenosine, capecitabine and other important intermediate preparation methods of 5′-deoxynucleoside drugs, specifically 1,2,3-O-tri-acetyl- Synthetic method of 5-deoxy-D-ribose. Background technique [0002] 1,2,3-O-tri-acetyl-5-deoxy-D-ribose is an important intermediate in the synthesis of nucleoside drugs. The current synthesis method of this intermediate is prepared by reacting inosine as raw material with acetic anhydride (Wang Chengju, Tang Donglin, patent publication number: CN200710019873.7, melting point 66-67°C). Because the iodine / imidazole / triphenylphosphine system is used to replace the 5-position hydroxyl of inosine ribose, the cost is high, and the acetylation bond breaking temperature is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/04
Inventor 朱仁发
Owner HEFEI UNIV
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