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Method for preparing 2-nitrine-1, 6-D-anhydro-sugars

A technology of inner ether sugar and 6-D-, which is applied in chemical instruments and methods, dehydrated sugar, sugar derivatives, etc., can solve the problems of environmental hazards for operators and unsuitability for industrialization, etc.

Inactive Publication Date: 2009-06-03
SHANGHAI INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires the use of highly toxic organotin compounds, which is very harmful to operators and the environment, and is not suitable for industrialization

Method used

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  • Method for preparing 2-nitrine-1, 6-D-anhydro-sugars

Examples

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preparation example Construction

[0021] (4) selective preparation of 3,4-position epoxy compound 5;

[0022] (5) Benzyl alcohol opens epoxy to prepare compound 6;

[0023] (6) Preparation of 2,3-position epoxy compound 7 under alkaline conditions;

[0024] (7) Azide opens epoxy to prepare compound 8;

[0025] (8) Benzyl protects the hydroxyl group to prepare the final product 9;

[0026] Wherein in step 1: fully acetylated D-glucose or L-glucose 1 and phenol are catalyzed by Lewis acid to prepare 2,3,4,6-tetraacetyl-phenyl glycoside; phenol or pentachloro Phenol, the dosage is 1 to 3 times of 1 (molar ratio); Lewis acid can be selected from halogenated boron, halogenated titanium, and halogenated tin, and fed in the calculated amount; the solvent is selected from C 1 -C 6 Monohalogen or polyhalogen alkanes, acetonitrile, dioxane, DMF, can be a single solvent or a mixed solvent, and the composition ratio is not specified; the reaction temperature is -10°C~100°C, the best reaction temperature is 0°C~ 30°C;...

Embodiment

[0035] Preparation of D-2,3,4,6-O-tetraacetylphenoside 2

[0036] Peracetyl-D-glucose 1 (390 g, 1 mol) was dissolved in 2 liters of dichloromethane, followed by adding phenol (141 g, 1.5 mol), triethylamine (51 g, 0.5 mol), under nitrogen protection, trifluoro Boronium ether (355 g, 2.5 mol) was slowly added dropwise to the above solution. After the dropwise addition was completed, the mixture was stirred at room temperature for 3 hours. The completion of the reaction was tracked and monitored by TLC. The reaction was quenched by adding 2 liters of saturated sodium bicarbonate solution, separated, and the aqueous phase was extracted with 2 liters of dichloromethane. The combined organic phases were dried, filtered and concentrated. A light yellow syrup 2 (360 g, 0.85 mol) was obtained with a yield of 85%.

[0037] Preparation of 2,3,4-trihydroxy-1,6-D-lactyl ether sugar 3

[0038]Light yellow syrup 2 (360 g, 0.85 mol) was placed in a 3L single-necked bottle, 2L of 1.3M KOH...

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Abstract

The invention relates to a method for preparing 2-nitrine-1, 6-D-anhydro-sugars, which is realized by the following steps: (1). absolute acetylation D-glucose or L-glucose (1) and phenol are reacted to prepare phthalic anhydride (2); (2). acetyl is removed under the condition of alkalescence and 1, 6-D-anhydro-sugars (3) are prepared; (3). Ts is used for selectively protecting, activating and preparing 2-4-hydroxide radical (4) by using steric clash in a lower temperature; (4). 3-4-epoxy compounds (5) is selectively prepared; (5) benzoic alcohol opening epoxy is used for preparing a compound (6); (6). a 2-3-epoxy compound (7) are prepared under the condition of alkalescence; (7) nitrine opening epoxy is used for preparing the compond; (8) phenmethyl protective hydroxide radical is used for preparing final products(9). The method has the beneficial effects of avoiding virulent organo-tin compound to be used and being suitable for industrial production.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a preparation method of 2-azido-1,6-D-endo-ether sugar. Background technique [0002] The 1,6-internal ether structure is used as a synthetic building block, which can not only be conveniently opened and converted into a sugar group protected by an acyl group at the anomeric position, but also obtain various donor building blocks (including Schmidt donors and glucosinolate donors, etc.) , to extend the sugar chain smoothly; on the other hand, the 1,6-endide structure can also be directly opened and transformed into a glycoside structure under appropriate conditions. 2-Azide-1,6-D-endosaccharide is the main raw material of many polysaccharide drugs. [0003] In the existing preparation methods, most of them start from fully acetylated glucose, go through bromoglycoside, glucosene, deacetylation, and then prepare inner ether sugar under the action of tributyltin oxide a...

Claims

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Application Information

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IPC IPC(8): C07H5/04C07H3/10
Inventor 刘烽
Owner SHANGHAI INSTITUTE OF TECHNOLOGY
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