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Method for preparing 6-alkoxy-2',3'-double deoxidated guanosine

A technology of dideoxyguanosine and guanosine, which is applied in the fields of sugar derivatives and organic chemistry, and can solve the problems of high synthesis cost and rare technical raw materials

Inactive Publication Date: 2007-04-11
GUANGZHOU YIPINHONG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is the problem of rare raw materials and high synthesis cost in the prior art

Method used

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  • Method for preparing 6-alkoxy-2',3'-double deoxidated guanosine
  • Method for preparing 6-alkoxy-2',3'-double deoxidated guanosine

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Embodiment Construction

[0011] The detailed technical process of the present invention is specifically described below.

[0012] 1. Preparation of N 2 -isobutyrylguanosine

[0013] Guanosine (20.0g, 770.67mmol), dry N,N-dimethylformamide (75ml), add hexamethyldisilazide (110ml), stir for 12.5 hours, cool to 10°C, add pyridine ( 100ml), isobutyric anhydride (180ml), reacted for 24 hours, cooled to 0°C, added methanol (200ml), reacted for 4 hours, concentrated to 100ml, added a mixture of n-hexane and ether (volume ratio was 1:1) ( 500ml), left overnight, filtered to obtain 24g of light yellow solid, yield 96%.

[0014] 2. Preparation of 2', 3'-dideoxy-2', 3'-didehydro-N 2 -isobutyrylguanosine

[0015] N 2 - Isobutyrylguanosine (6.74g, 20mmol), dry acetonitrile (80ml), add 0.4ml of water, add acetoxyisobutyryl bromide, stir at room temperature for 1 hour, filter, add ethyl acetate (200ml) to the filtrate, wash with water To neutrality, dry with anhydrous magnesium sulfate and concentrate to 50ml,...

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Abstract

A process for preparing 6-alkoxy-2',3'-dideoxyguanosine from guanosine as initial raw material includes such steps as synthesizing 2',3'-deoxy-2',3'-dehydro-guanosine, ordinary-pressure reducing by 10% Pd / C, alkylation, preparing N2-isobutyryl guanosine, preparing 2',3'-dideoxy-2',3'-dihydro-N2-isobutyryl guanosine, preparing 2',3'-dideoxy-guanosine, preparing 5'-acetoxy-2',3'-dideoxy-guanosine, preparing 5'-acetoxy-6-chloro-2',3'-dideoxy-guanosine, and preparing target product. Advantages include mild reaction condition, low raw material price etc.

Description

technical field [0001] The present invention relates to a preparation method of a compound, in particular to a preparation method of 6-alkoxy-2', 3'-dideoxyguanosine. Background technique [0002] The 2' and 3' deoxynucleosides can be incorporated into the DNA chain by DNA polymerase as a substrate. Due to the loss of the 3' hydroxyl group, the continued extension of the DNA chain is terminated. This principle is widely used in the design of antiviral drugs. Such as Zidovudine (AZT), Zalcitabine (Zalcitabine, DDC), Stavudine (Stavudine, D4T), Didannosine (Didannosine, ddI) [Mitsuya H. et al., Science 1990, 249, 1533-44; Huryn D.M. et al., Chem.Rev.1992, 92, 1745; De Clereq E. et al., Nucleoside Nucleotide 1994, 13, 1271-95; De Clereq E. et al., J.Med.Chem. 1995, 38, 2491-517; Mansour T.S. et al., Current Pharmac. Design 1997, 3, 227] [0003] Structural formula is 6-alkoxy-2' of formula (1), the synthetic method of 3'-dideoxyguanosine has be...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/16
Inventor 姚其正黄海燕李战刘经辉
Owner GUANGZHOU YIPINHONG PHARMA