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A kind of preparation method of 2-hydroxygulose receptor derivative, bleomycin disaccharide and its precursor

A technology of hydroxygulose and pyranoguloside, which is applied in the field of medicine and chemical industry, can solve the problems of unsuitable for industrialization, high cost, and scarce sources of natural L-gulose, and achieve easy control of conditions, high yield, highly operable effect

Active Publication Date: 2021-08-10
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Based on this, the purpose of the present invention is to overcome the above-mentioned weak points of the prior art and provide a kind of preparation method of 2-hydroxygulose, solve the difficult problems such as natural L-gulose source is rare, cost is too high and unsuitable for industrialization

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  • A kind of preparation method of 2-hydroxygulose receptor derivative, bleomycin disaccharide and its precursor
  • A kind of preparation method of 2-hydroxygulose receptor derivative, bleomycin disaccharide and its precursor
  • A kind of preparation method of 2-hydroxygulose receptor derivative, bleomycin disaccharide and its precursor

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Embodiment 1

[0052] An embodiment of the preparation method of the 2-hydroxygulose receptor derivative of the present invention comprises the following steps:

[0053] (1) Preparation of benzyl-2,3-dihydroxy-4,6-O-benzylidene-β-D-galactopyranoside (G-3)

[0054] The G-3 structural formula is

[0055] ① Preparation of benzyl-β-D-galactopyranoside (G-2)

[0056] The G-2 structural formula is

[0057] Under the protection of nitrogen, dissolve 180g of β-D-galactopyranose (1mol) into 100mL of benzyl alcohol, add 1 g of p-toluenesulfonic acid to catalyze it at the same time, react overnight at 150°C, distill out the benzyl alcohol under reduced pressure, and use anhydrous methanol 235 g of benzyl-β-D-galactopyranoside were obtained by recrystallization, with a yield of 87.1%.

[0058] 1 H NMR (400MHz, CDCl 3 )δ7.50-7.20(m,5H),4.95(d,J=12Hz,1H),4.68(d,J=12Hz,1H),4.43(d,J=8.0Hz,1H),3.90-3.71( m,3H),3.68-3.40(m,3H).

[0059] ②Under the protection of nitrogen, add 27.5mL of benzene Form...

Embodiment 2

[0078] An embodiment of the preparation method of the 2-hydroxygulose receptor derivative of the present invention comprises the following steps:

[0079] (1) Preparation of benzyl-2,3-dihydroxy-4,6-O-benzylidene-β-D-galactopyranoside (G-3)

[0080] ① Preparation of benzyl-β-D-galactopyranoside (G-2)

[0081] Under the protection of nitrogen, dissolve 180g of β-D-galactopyranose (1mol) into 100mL of benzyl alcohol, add 1 g of p-toluenesulfonic acid to catalyze it at the same time, react overnight at 150°C, distill out the benzyl alcohol under reduced pressure, and use anhydrous methanol 235 g of benzyl-β-D-galactopyranoside were obtained by recrystallization, with a yield of 87.1%.

[0082] ②Under the protection of nitrogen, put 40.5g of benzyl-β-D-galactoside (150mmoL) and 2.85g of camphorsulfonic acid in dry dimethyl sulfoxide (DMSO) (250mL) solution, and drop 27.5mL of Benzaldehyde, the reaction mixture was stirred under reduced pressure for 4h, and the reaction temperatu...

Embodiment 3

[0092] An embodiment of the preparation method of the 2-hydroxygulose receptor derivative of the present invention comprises the following steps:

[0093] (1) Preparation of benzyl-2,3-dihydroxy-4,6-O-benzylidene-β-D-galactopyranoside (G-3)

[0094] ① Preparation of benzyl-β-D-galactopyranoside (G-2)

[0095] Under the protection of nitrogen, dissolve 180g of β-D-galactopyranose (1mol) into 100mL of benzyl alcohol, add 1 g of p-toluenesulfonic acid to catalyze it at the same time, react overnight at 150°C, distill out the benzyl alcohol under reduced pressure, and use anhydrous methanol 235 g of benzyl-β-D-galactopyranoside were obtained by recrystallization, with a yield of 87.1%.

[0096] ②Under nitrogen protection, add 27.5 mL of benzaldehyde dropwise to a solution of 40.5 g of benzyl-β-D-galactoside (150 mmoL) and 2.85 g of Dowex 50WX8-200 in dry diglyl dimethyl ether (250 mL) Dimethyl acetal (180mmoL), the reaction mixture was stirred under reduced pressure for 4h, and ...

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Abstract

The invention discloses a preparation method of 2-hydroxygulose acceptor derivatives, which comprises protecting benzyl-β-galactoside benzyl fork group, inversion of 3-position configuration, deacetylation and selective acetylation series of reactions. At the same time, the invention also discloses a method for preparing bleomycin disaccharide and its precursor by using the 2-hydroxygulose receptor derivative prepared by the method as the receptor. The preparation method of the 2-hydroxygulose acceptor derivative of the present invention solves the defects of rare natural L-gulose source, high cost, unsuitable for industrialization, etc., and simultaneously solves the problem of bleomycin disaccharide and its precursor yield Low, poor operability and repeatability of the reaction, unsuitable for industrialization and other problems. It has the advantages of cheap and easy-to-obtain raw materials, high yield, strong operability, easy control of conditions, industrial scale-up, high efficiency and low cost.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a preparation method of 2-hydroxygulose receptor derivatives, bleomycin disaccharide and its precursors. Background technique [0002] Bleomycin (BLM) is a glycopeptide antitumor antibiotic drug used in the first-line clinical treatment of tumors. It is mainly used to treat squamous cell carcinoma, Hodgkin's malignant lymphoma, cervical cancer and testicular cancer. Streptomyces verticillus. The BLM structure consists of three parts: 1) 5 amino acids composed of pyrimidine-imidazole structure; 2) 1 side chain containing bithiazole amino group; 3) 1 unique disaccharide structure. A large number of studies have shown that the pyrimidine-imidazole structure is the key part of the anti-tumor effect of BLM, which can selectively oxidize and cleave the 5'-GC-3' and 5'-GT-3' sequences in DNA, thereby exerting anti-tumor activity; The structure can be...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/18C07H13/12C07H1/00
CPCC07H1/00C07H13/12C07H15/18
Inventor 周文李茂林袁思思
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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