Method for producing a 2-deoxy-L-ribose

一种核糖、烷基的技术，应用在2－脱氧－L－核糖的制备领域，能够解决使用昂贵、高毒性试剂、艰难分离和纯化等问题，达到容易分离和纯化的效果

Inactive Publication Date: 2005-09-14
SAMCHULLY PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] But in these methods, expensive or highly toxic reagents are used; difficult isolation and purification are required; the overall yield is low; all these are obstacles for large-scale synthetic application

Method used

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  • Method for producing a 2-deoxy-L-ribose
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  • Method for producing a 2-deoxy-L-ribose

Examples

Experimental program
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Effect test

Embodiment approach 1

[0047] Protection: Preparation of 2-deoxy-1-O-butyl-D-ribose

[0048] To cooled butanol containing 3% HCl (56.4 mL), 2-deoxy-D-ribose (robse) (10 g) was added and stirred at -2°C for 16 hours. Keeping the temperature below 10°C, the reaction mixture was neutralized with triethylamine and stirred at 20°C to 25°C. The mixture was filtered and washed with acetone (20 mL). The combined filtrate and washing solution were concentrated and used for further reaction without purification.

Embodiment approach 2

[0050] Activation of the 3-4-OH group: Preparation of 2-deoxy-1-O-butyl-3,4-bis(p-toluenesulfonyl)-D-ribose

[0051]Below 30°C, to the solid of 2-deoxy-1-O-butyl-D-ribose obtained in Embodiment 1, gradually add pyridine (36 mL), p-toluenesulfonyl chloride, and at 27°C to 30°C The mixture was stirred for 20 hours. The reaction mixture was heated to 75±2°C and stirred for 2 hours. After the reaction was completed, the mixture was cooled to 15°C to 20°C, and pure water (30 mL) was added, and the resulting mixture was extracted twice with ethyl acetate (30 mL). The extract was concentrated, and ethanol and isopropanol were added. The solution was cooled, filtered and dried to give 2-deoxy-1-O-butyl-3,4-di-(p-toluenesulfonyl)-D-ribose as a solid (23 g).

Embodiment approach 3

[0053] Conversion from D-form sugars to L-form sugars: 2-deoxy-1-O-butyl-3-benzoyl-L-ribose and 2-deoxy-1-O-butyl-4-benzoyl- Preparation of L-ribose

[0054] To the compound (20 g) obtained in Embodiment 2, were added n-butanol (7 mL), water (4.4 mL), N,N-dimethylformamide (27.6 mL) and potassium benzoate (21.2 g) , and the reaction mixture was heated to 115° C. for 8 hours. After the reaction mixture was concentrated, water and ethyl acetate were added to the separated organic and aqueous layers. After concentration of the organic layer, the residue was mixed with water and evaporated again to effectively concentrate the dimethylformamide. The residue was used for the next reaction.

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Abstract

The present invention relates to a economic synthetic method of 2-deoxy-L-ribose from 2-deoxy-D-ribose with easy reaction, separation and purification. The present invention consists of four(4) steps including protection, activation 3-and 4-OH groups, inversion and deprotection step. In respect to the cost for equipment, reagent and operation, by the present invention, 2-deoxy-L-ribose can be produced more economically because the invention uses 2-deoxy-L-ribose which is abundant in nature and easily synthesized from D-glucose, and adopt simple and yielding process.

Description

technical field [0001] The present invention relates to a method for synthesizing a compound having the following compound (1), more specifically, to a method for large-scale production and cost-saving synthesis of compound (1) from 2-deoxy-L-ribose with easy reaction, separation and purification method. [0002] [0003] Compound (1) Background technique [0004] Recently, natural or modified L-nucleosides are attracting attention as antiviral agents. Some L-nucleosides such as L-thymidine, L-2'-thiocytidine (3TC) and L-2',3'-dideoxycytidine (L-ddC) are more Less toxic and have better antiviral activity. In addition, L-nucleosides have a good effect in the treatment of anti-sensitive oligonucleotides. [0005] For the reasons above, many attempts have been made to efficiently synthesized L-nucleosides which are not available as natural products. These attempts have focused on the economical and large-scale preparation of derivatives of L-sugars, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H3/02C07H3/08
CPCC07H1/00C07H3/08C07H3/02
Inventor 姜在声尹美泓李相大全炳瓒申姃娥
Owner SAMCHULLY PHARM CO LTD
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