Method of preparing 2-deoxy-L-ribose

A technology of ribose and equation, which is applied in the field of preparation of 2-deoxy-L-ribose, can solve the problems of limited source of raw materials, difficulty in large-scale production, long synthetic route, etc., and achieves easy-to-obtain raw materials, mild conditions and high yield Effect

Inactive Publication Date: 2008-02-20
XIAMEN UNIV
View PDF0 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some of these methods have long synthetic routes and low efficiency, and so

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
  • Method of preparing 2-deoxy-L-ribose
  • Method of preparing 2-deoxy-L-ribose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] First prepare (2) from D-(-)-ribose according to the literature method (V. Jaeger, B. Hafele, Synthesis, 1987, 9, 801), and then prepare 2-deoxy-L-ribose according to the following steps.

[0027] In a 25mL round bottom flask, weigh NaH (334mg, 8.34mmol), add anhydrous THF (11.0mL), cool the reaction system to 0°C, add dropwise (2) (584mg, 3.69mmol) dissolved in anhydrous THF (3.0mL) the formed solution, after addition, stirred at 0°C for 30min, added Bu 4 NI (51mg, 0.14mmol), BnBr (1.1mL, 9.04mmol) was added dropwise, the temperature was gradually raised to room temperature and stirring was continued for 18h, then water (5.0mL) was added, the organic phase was separated, and the aqueous phase was extracted with diethyl ether (3×5mL ). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by flash silica gel column chromatography to obtain (3)...

Embodiment 2

[0032] Similar to Example 1, the difference is that the amount of sodium hydride in the preparation (3) step is 1.8 molar multiples of (2), Bu 4 The consumption of NI is 10% mole; The consumption of palladium chloride and cuprous chloride is respectively 0.1 and 1.0 mole multiples of (3) in the preparation (4) step, and the ratio of the two in the mixed solvent of DMF and water is 6: 2. The reaction temperature is 75°C and the reaction time is 12h; the concentration of (4) in tetrahydrofuran in the step (5) of preparing benzyl 2-deoxy-L-ribose is 0.15mol / L; preparing 2-deoxy-L-ribose (6) The amount of palladium carbon in the step is 0.2 mole multiple of (5), the concentration of (5) in methanol solution of 10% formic acid is 0.35mol / L, and the reaction time is 4h.

Embodiment 3

[0034] Similar to Example 1, the difference is that the concentration of (2) added in the preparation (3) step is 0.6mol / L; the consumption of palladium chloride and cuprous chloride in the preparation (4) step is respectively 0.2 of (3) and 1.3 molar multiples, the ratio of the two in the mixed solvent of DMF and water is 6: 2, (3) the concentration in DMF and water solvent is 0.7mol / L, the reaction temperature is 75 ℃, and the reaction time is 12h; the preparation of benzyl The concentration of (4) in tetrahydrofuran in the base 2-deoxy-L-ribose (5) step is 0.15mol / L, and the consumption of palladium carbon in the preparation of 2-deoxy-L-ribose (6) step is 0.2% of (5). Molar multiple, (5) The concentration in methanol solution of 10% formic acid is 0.35mol / L, and the reaction time is 4h.

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

A preparation method of a 2-dioxidation-L-ribose relates to a non-natural deoxidation pentose. The invention provides the preparation method that takes D-(-)-ribose (1) as raw material and has simple technology, high optical activity and yield of the 2-dioxidation-L-ribose. (2S, 3R)-2, 3-O- isopropylidene-4-pentenol (2) is prepared through the raw material (1) by a literature method, hydroxide radical of the first carbon in (2) is protected to get (3R, 4S)-3, 4-O-isopropylidene-5- benzyloxy-4-pentene(3), then (3R,4S)-3, 4-O- isopropylidene-5- benzyloxy pentanal (4) is prepared through preferred oxidation at the end of the double linkage (3) in the existence of palladium chloride and cuprous chloride, acetonide protecting group in (4) is removed through catalysis of acid and phenmethyl 2-dioxidation-L-ribose (5) is obtained through cyclization, finally the 2-dioxidation-L-ribose (6) is prepared after the phenmethyl is removed through catalysis.

Description

technical field [0001] The invention relates to a non-natural deoxygenated five-carbon sugar, in particular to a preparation method of 2-deoxy-L-ribose. Background technique [0002] 2-Deoxy-L-ribose is a non-natural deoxy five-carbon sugar compound, it is an important intermediate in the synthesis of non-natural L-nucleoside drugs, and is used in the study of protein-DNA interaction, so in nuclear The medical application of glycoside derivatives has important significance and application value. However, since 2-deoxy-L-ribose is a non-natural ribose, its source is mainly obtained through chemical synthesis. However, since 2-deoxy-L-ribose contains 3 chiral centers, how to control the stereoselectivity of the synthesis process and ensure the high optical purity of the product is a difficult point in the synthesis of this compound. Therefore, it is of great significance to develop an efficient, practical, and optically pure 2-deoxy-L-ribose synthesis route. [0003] The me...

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
IPC IPC(8): C07H3/08
CPCY02P20/55
Inventor 陈安齐崔兰州
Owner XIAMEN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap