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A kind of synthetic method of regioselective acetylated methyl-d-pyranoside

An acetylated methyl group and regioselectivity technology, applied in the fields of fine chemicals and sugar chemical synthesis, can solve problems such as environmental pollution and complicated operation, and achieve the effects of reducing reaction toxicity, low cost and mild reaction conditions

Inactive Publication Date: 2015-11-04
NORTHWEST A & F UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to provide a synthetic method for regioselective acetylation of methyl-D-pyranoside, aiming to solve the problem of using high boiling point in the process of regioselective acetylation of methyl-D-pyranoside in the prior art. , highly toxic organic reagents as solvents, serious environmental pollution, cumbersome operations, etc.

Method used

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  • A kind of synthetic method of regioselective acetylated methyl-d-pyranoside
  • A kind of synthetic method of regioselective acetylated methyl-d-pyranoside
  • A kind of synthetic method of regioselective acetylated methyl-d-pyranoside

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Embodiment 1

[0020] At 60°C, use 200 μL of water as a solvent, mix 50 mg (1.0 eq) of methyl-α-D-glucopyranoside and 114 μL (1.2 eq) of 25% tetramethylammonium hydroxide solution, and then add 1 - Acetyl imidazole 85.9mg (3.0eq), after 18 hours of reaction, the solvent was removed under reduced pressure, and the 6-position acetylated methyl-α-D-glucopyranoside derivative was obtained by column separation, and the column separation yield was 52%.

Embodiment 2

[0022] At 60°C, use 200 μL of water as a solvent, mix 50 mg (1.0 eq) of methyl-β-D-glucopyranoside and 114 μL (1.2 eq) of 25% tetramethylammonium hydroxide solution, and then add 1 -Acetylimidazole 85.9mg (3.0eq), after reacting for 14h, the solvent was removed under reduced pressure, and the 6-position acetylated methyl-β-D-glucopyranoside derivative was obtained by column separation, and the column separation yield was 56%.

Embodiment 3

[0024] At 60°C, use 200 μL of water as a solvent, add 50 mg (1.0 eq) of methyl-α-D-galactopyranoside and 114 μL (1.2 eq) of tetramethylammonium hydroxide (25% aqueous solution), Then add 85.9 mg (3.0 eq) of 1-acetylimidazole, react for 18 hours, remove the solvent under reduced pressure, and obtain 6-acetylated methyl-α-D-galactopyranoside derivatives through column separation. rate 59%.

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Abstract

A disclosed synthetic method for regioselectively-acetylated methyl-D-pyranosides comprises: at 60 DGE C, taking water as a solvent, mixing a methyl-D-pyranoside and tetramethylammonium hydroxide (an aqueous solution with a concentration of 25%), adding 1- acetylimidazole, reacting for 14-18 h, removing solvent under a reduced pressure, and separating by a column to obtain the glucoside derivative acetylized at 6th position. The method employs water as a solvent to replace pyridine or DMF in traditional methods, so that the reaction toxicity is substantially reduced, and the column separation yield is basically 52% or more; and additionally, the provided efficient green method for acetylizing methyl-D-pyranosides is not only simple in operation, mild in conditions and low in cost, but also green and environment-friendly, is accord with the develop requirements of current social, and has good application and develop prospect.

Description

technical field [0001] The invention belongs to the field of fine chemicals and sugar chemical synthesis, and in particular relates to a synthesis method of regioselective acetylated methyl-D-pyranoside. Background technique [0002] In organic synthesis, selective protection of reactants with multiple sites of similar reactivity has always been a severe challenge for synthetic chemists. Especially in the synthesis of many oligosaccharides, polysaccharides, glycopeptides, sugar esters and other compounds with biological significance and synthetic value, due to the presence of multiple hydroxyl groups with similar properties in sugar molecules, in order to positionally introduce glycosidic bonds on sugar rings And various functional groups, other hydroxyl groups on the sugar ring must be selectively protected. Therefore, the regioselective protection of sugar hydroxyl groups has always been one of the research hotspots in the chemical synthesis of sugars. [0003] At presen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/04C07H1/00
Inventor 裴志超卢玉超裴玉新韦鹏辛晓婷徐恒福
Owner NORTHWEST A & F UNIV
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