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Preparation method of 2-deoxy-beta-D-glucopyranosyl triazole compound

A technology of glucopyranose and base triazole, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., and achieves the effects of green environmental protection yield, mild reaction conditions, and simple reaction operation.

Inactive Publication Date: 2011-12-14
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of a series of glycosyltriazoles with high yield by using three-membered ring carbohydrates as substrates, CuI as a catalyst, and PEG-400 as a solvent has not been reported in the literature.

Method used

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  • Preparation method of 2-deoxy-beta-D-glucopyranosyl triazole compound
  • Preparation method of 2-deoxy-beta-D-glucopyranosyl triazole compound
  • Preparation method of 2-deoxy-beta-D-glucopyranosyl triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Add 1,2-deoxy-3,4,6-tri-O-benzyl-7-C-acetyl-α-D-glucopyranose (47.2mg, 0.1mmol) to a 10mL reaction flask And sodium azide (9.8mg, 0.15mmol), then add PEG-400 (1mL) to dissolve, and stir at 80°C for 10h. Phenylacetylene (13.5 μL, 0.12 mmol) and CuI (1.9 mg) were then added at room temperature. Stir at room temperature, and TLC detects that the reaction is complete. Ethyl acetate was added for extraction (5mL×3), and the extract was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=3:1~2:1) to obtain 1-(2′-C- Acetylmethyl-2'-deoxy-3',4',6'-tri-O-benzyl-β-D-glucopyranose)-4-phenyl-1,2,3-triazole 50.6mg, Yield 82%. (c 0.1, CHCl 3 ); mp: 137-138°C; 1 H NMR (600MHz, CDCl 3 ):δ H 7.98(s, 1H), 7.86(d, J=7.2Hz, 2H), 7.46(t, J=7.7Hz, 2H), 7.41-7.22(m, 17H), 5.93(d, J=10.2Hz, 1H ), 5.00 (d, J = 11.6Hz, 1H), 4.87 (d, J = 10.8Hz, 1H), 4.70 (d, J = 10.8Hz, 1H), 4.64 (dd, J = 11.9, 4.6Hz, 2H ), 4.57(d, J=12.2Hz, ...

Embodiment 2

[0032]Example 2: Add 1,2-deoxy-3,4,6-tri-O-benzyl-7-C-acetyl-α-D-glucopyranose (47.2mg, 0.1mmol) to a 10mL reaction flask And sodium azide (9.8mg, 0.15mmol), then add PEG-400 (1mL) to dissolve, and stir at 80°C for 10h. Then, 2-methylphenylacetylene (15.0 μL, 0.12 mmol) and CuI (1.9 mg) were added at room temperature. Stir at room temperature, and TLC detects that the reaction is complete. Ethyl acetate was added for extraction (5mL×3), and the extract was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=3:1~2:1) to obtain 1-(2′-C- Acetylmethyl-2'-deoxy-3',4',6'-tri-O-benzyl-β-D-glucopyranose)-4-(2'-methylphenyl)-1,2, 3-triazole 48.0 mg, yield 76%. (c 0.3, CHCl 3 ); mp: 115°C; 1 H NMR (600MHz, CDCl 3 ):δ H 7.84(s, 1H), 7.78-7.72(m, 1H), 7.38-7.19(m, 19H), 5.87(d, J=10.2Hz, 1H), 4.98(d, J=11.6Hz, 1H), 4.84 (d, J=10.8Hz, 1H), 4.68(d, J=10.8Hz, 1H), 4.65-4.58(m, 2H), 4.54(d, J=12.2Hz, 1H), 3.88(t, J= 9.0Hz, 1H), 3.8...

Embodiment 3

[0033] Example 3: Add 1,2-deoxy-3,4,6-tri-O-benzyl-7-C-acetyl-α-D-glucopyranose (47.2mg, 0.1mmol) to a 10mL reaction flask And sodium azide (9.8mg, 0.15mmol), then add PEG-400 (1mL) to dissolve, and stir at 80°C for 10h. Then, 3-chlorophenylacetylene (14.3 μL, 0.12 mmol) and CuI (1.9 mg) were added at room temperature. Stir at room temperature, and TLC detects that the reaction is complete. Ethyl acetate was added for extraction (5mL×3), and the extract was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=3:1~2:1) to obtain 1-(2′-C- Acetylmethyl-2′-deoxy-3′,4′,6′-tri-O-benzyl-β-D-glucopyranose)-4-(3″-chlorophenyl)-1,2,3 - Triazole 48.8 mg, yield 75%. (c 0.4, CHCl 3 ); mp: 159°C; 1 H NMR (600MHz, CDCl 3 ):δ H 7.94(s, 1H), 7.84(s, 1H), 7.70(d, J=7.5Hz, 1H), 7.38-7.18(m, 17H), 5.88(d, J=10.2Hz, 1H), 4.97(d , J=11.6Hz, 1H), 4.84(d, J=10.8Hz, 1H), 4.67(d, J=10.8Hz, 1H), 4.61(dd, J=11.9, 6.3Hz, 2H), 4.54(d , J=12.2Hz, 1H...

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Abstract

The invention belongs to the technical fields of organic chemistry and pharmaceutical chemistry, and specifically relates to a preparation method of a 2-deoxy-beta-D-glucopyranosyl triazole compound. According to the invention, a 1,2-deoxy-7-C-acetyl-alpha-D-glucopyranose derivative is subject to a reaction with sodium azide, such that 2-deoxy-beta-D-glucopyranosyl nitrine is produced. Terminal alkyne and a catalyst copper iodide are added to the same reactor, and the 2-deoxy-beta-D-glucopyranosyl triazole compound is produced through a reaction. According to the invention, a one-pot method is adopted, and the method has advantages of mild reaction condition, simple reaction operation, green and environment-protective solvent, and high yield.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and medicinal chemistry, and specifically relates to a preparation method of 2-deoxy-β-D-glucopyranosyl triazole compounds. Background technique [0002] Glycotriazole compounds are often used in drug development research, such as: Compound 1 has a highly selective inhibitory effect on human α-1,3-fucosyltransferase (J.Am.Chem.Soc.2003, 125 , 9588-9589); Compound 2 was used to synthesize uridine diphosphate—a sugar analogue (Carbohydrate Research 2009, 344, 586-591); Compound 3, 4 had weak Trypanosoma cruzi trans-sialidase ( TcTS) inhibition, can be used as a substrate receptor by Trypanosoma cruzi trans-sialidase (Bioorg.Med.Chem.2010, 18, 2412-2427); Compound 5 has better yeast α-glucosidase inhibitory activity (Carbohydrate Research 2010, 345, 1123-1134); Compound 6 was studied as a protein tyrosine phosphatase 1b (PTP1B) inhibitor (Carbohydrate Research 2011, 346, 140-145), indicati...

Claims

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Application Information

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IPC IPC(8): C07H19/056C07H1/00
Inventor 邵华武汤琴
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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