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Method for production of furanose derivative

A manufacturing method and compound technology, applied in the direction of sugar derivatives, sugar derivatives, esterified saccharides, etc.

Active Publication Date: 2009-12-02
API CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For D-DTAR, its β-anomer is a solid, while its α-anomer is an oily substance. Therefore, in the process of conversion from ribose and the separation of by-products and the purification of the target product, by The β-anomer that can be purified by recrystallization or washing with an inexpensive solvent is advantageous for industrial production, but since the obtained crude D-DTAR has an anomer ratio β / α=3 / 1, it is not A method for efficiently obtaining target β-anomers

Method used

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  • Method for production of furanose derivative
  • Method for production of furanose derivative
  • Method for production of furanose derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A1

[0108] (1) Synthesis of 1-O-methyl-L-ribofuranose

[0109] L-ribose (20.0 g, 132 mmol) and methanol (226 g) were added to a 1000 mL flask, and concentrated sulfuric acid (1.49 g, 0.11 equivalent) dissolved in methanol (21.2 g) was slowly added dropwise. After reacting at room temperature for 5 hours, sodium acetate (2.40 g) was added for neutralization, and it was concentrated under reduced pressure. 31.18 g of crude 1-O-methyl-L-ribofuranose was obtained in the form of white turbid oil.

[0110] 1 H-NMR (400MHz, D 2 Od): δ (β-anomeric object) 3.38 (s, 3H), 3.57-3.62 (m, 1H), 3.76-3.80 (m, 1H), 3.99-4.03 (m, 2H), 4.13-4.16 (m , 1H), 4.89 (d, J = 1.0 Hz, 1H) (α-anomeric) 3.42 (s, 3H), 3.63-3.75 (m, 2H), 3.98-4.11 (m, 3H), 4.98 (d , J=4.5Hz, 1H)

[0111] (2) Synthesis of 2,3,5-tri-O-benzoyl-1-O-methyl-L-ribofuranose

[0112] Add 31.18g of the crude 1-O-methyl-L-ribofuranose synthesized in (1) above, toluene (175mL), 25wt.% aqueous sodium hydroxide solution (111mL), and tetra-n-butyl...

Embodiment B1

[0122] (1) Synthesis of 2,3,5-tri-O-acetyl-1-O-methyl-L-ribofuranose

[0123] A 500-ml four-necked flask was replaced with nitrogen, 60.0 g (400 mmol) of L-ribose and 300 ml of methanol were added thereto, cooled to 5°C on an ice bath, and 5.60 g of concentrated sulfuric acid was added. Then, the temperature was raised to room temperature, and after stirring for 4 hours, 14.7 g of sodium acetate was added and stirred for 30 minutes. Methanol was distilled off from the reaction mixture under reduced pressure, 120 mol of acetic acid was added and distilled off under reduced pressure. It was confirmed by NMR that methanol was not present, and 1.7 equivalents of acetic acid remained with respect to the ribose derivative, and this was directly used in the next step.

[0124] To the obtained reaction mixture, 11.9 g of acetic acid and 151 g of acetic anhydride were added so that the acetic acid was 5 equivalents to the ribose derivative, and the temperature was raised to 100° C. and sti...

Embodiment B2

[0129] Synthesis of 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

[0130] A 100 ml four-necked flask was replaced with nitrogen, and 11.32 g of 2,3,5-tri-O-acetyl-1-O-methyl-L-ribofuranose obtained in (1) of Example B1 was added to it. As L-ribose (equivalent to 40 mmol) and 20 ml of diisopropyl ether, kept at 0±5°C on an ice bath, and 8.17 g (2.0 equivalents) of acetic anhydride was added. While stirring on an ice bath, 3.2 g (0.8 equivalent) of concentrated sulfuric acid was added dropwise at an internal temperature of 0±5°C. After stirring on an ice bath for 3.5 hours, it was kept in the refrigerator overnight and kept below 5°C. While stirring on an ice bath, 7.87 g of sodium acetate was added, and the mixture was stirred on an ice bath for 30 minutes. At room temperature, 120 ml of ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added until the aqueous layer was neutralized, and liquid separation was performed. The aqueous layer was extracted with 120...

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Abstract

An object of the present invention is to provide a industrially appropriate method for producing the beta-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein beta-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and / or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.

Description

Technical field [0001] The present invention relates to a method for producing furanose derivatives, and in more detail, it relates to the anomeric hydroxyl group in the production of acylated furanose α, β-mixtures to make β-anomers (anomer ) A method of crystallizing out in the reaction system to increase the yield of β-anomers and to produce them efficiently. The furanose derivative prepared in the method of the present invention can be effectively used as an intermediate for the synthesis of nucleic acid derivatives as pharmacologically active substances. Background technique [0002] In the case of using sugars as intermediates for medical and agricultural chemicals, the production is performed stereoselectively. In this case, from an industrial point of view, it is preferable to suppress the generation of off-target stereoisomers and efficiently produce the target stereoisomers. body. Furthermore, since precursors of furanose and / or furanose derivatives as starting material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04
CPCC07H15/04C07H13/04C07H13/08C07D307/62
Inventor 桂田学佐佐木智子中岛泰子兴村信夫
Owner API CO LTD
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