Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of beta-thymidine

A technology for thymidine and intermediates, which is applied in the production of β-thymidine and fine chemical industry, can solve the problems of low yield and no obvious improvement in raw material utilization, achieve low impurity content in products, reduce production costs and labor The effect of low strength and yield

Active Publication Date: 2014-12-03
安徽金太阳生化药业有限公司 +1
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the utilization rate of raw materials has not been significantly improved, and the yield is not high.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of beta-thymidine
  • Preparation method of beta-thymidine
  • Preparation method of beta-thymidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 44.9 g (0.1 mol) of di-tert-butylsilyl bis(trifluoromethanesulfonic acid) dropwise into 90 ml pyrrole dissolved with 25.8 g 5-methyluridine (0.1 mol), react at 0°C for 1 hour, then Raise the temperature to 25°C and continue the reaction for 1 hour. After no raw material was detected by TLC, it was cooled to room temperature, the solvent was distilled off under reduced pressure, washed and dried to obtain 38.7 g of colorless crystal powder which was intermediate I, and the yield was 98.5%.

[0032]

[0033] 1 HNMR (CD 3 SOCD 3 ,400MHz) δ (ppm): 1.01(s,9H),1.10(s,9H),1.95(s,3H),3.65(t,1H),3.75-3.95(d,2H),4.25-4.33(t ,1H),4.40(t,1H),5.85-5.93(d,1H),7.74(s,1H),11.25(s,1H)

Embodiment 2

[0035] Add 40g (0.1mol) of dimethylsilylbis(trifluoromethanesulfonic acid) dropwise into 100ml pyridine dissolved with 25.8g 5-methyluridine (0.1mol), react at 5°C for 1 hour, then raise the temperature to 25°C The reaction was continued for 1 hour at ℃, no raw material was determined by TLC, and then cooled to room temperature, the solvent was distilled off under reduced pressure, washed and dried to obtain 38.7 g of colorless crystal powder which was intermediate I, and the yield was 98.5%.

[0036]

[0037] 1 HNMR (CD 3 SOCD 3 ,400MHz) δ (ppm): 0.98(s,6H), 1.95(s,3H), 3.65(t,1H), 3.75-3.91(d,2H), 4.25-4.33(t,1H), 4.40(t ,1H),5.85-5.93(d,1H),7.74(s,1H),11.25(s,1H)

Embodiment 3

[0039] Add 41.3g (0.1mol) of diethylsilylbis(trifluoromethanesulfonic acid) dropwise into 100ml pyridine dissolved with 25.8g 5-methyluridine (0.1mol), react at 5°C for 1 hour, then heat up to The reaction was continued for 1 hour at 25°C. After no raw material was determined by TLC, it was cooled to room temperature, the solvent was distilled off under reduced pressure, washed and dried to obtain 39.1 g of colorless crystal powder, which was intermediate I, and the yield was 98.6%.

[0040]

[0041] 1 HNMR (CD 3 SOCD 3 ,400MHz) δ (ppm): 1.03(dd,4H), 1.15(t,6H), 1.94(s,3H), 3.65(t,1H), 3.75-3.95(d,2H), 4.25-4.33(t ,1H),4.40(t,1H),5.85-5.93(d,1H),7.74(s,1H),11.25(s,1H)

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of beta-thymidine. The method includes using 5-methyluridine as a raw material to react with a silica-based protection reagent so as to protect two hydroxyl groups, then the mixture reacts with a halogenated reagent, and finally the mixture is subjected to reduction, hydrogenation and deprotection to prepare the beta-thymidine. According to the preparation method of the beta-thymidine, by means of a silica-based protection method, propionyl chloride is prevented from being used in the reaction process so that the yield is effectively improved, corrosion on devices is avoided, and the total yield reaches above 90%.

Description

1. Technical field [0001] The invention relates to a method for producing β-thymidine with 5-methyluridine as a starting material, which belongs to fine chemical technology. 2. Background technology [0002] β-thymidine is a key intermediate in the synthesis of anti-AIDS drugs "stavudine" and "zidovudine", and there is no natural product. At present, artificial synthesis methods include biosynthesis and chemical synthesis. Biosynthesis requires high production equipment and high cost. At present, the preparation of β-thymidine is mainly based on chemical synthesis. [0003] The early β-thymidine synthesis method mainly used ribose and deoxyribose as starting materials, the cost of raw materials was high, and toxic reagents such as tin and mercury were needed in the production process, which greatly limited the industrialization process of β-thymidine. At present, the relatively perfect production method of β-thymidine is: use 5-methyluridine as raw material to synthesize ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/073C07H1/00
Inventor 朱满洲汪恕欣孟祥明宁中伟徐三能强泽明
Owner 安徽金太阳生化药业有限公司