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Batch synthesis method of epilactose

A synthesis method and batch technology are applied in the field of batch synthesis of epilactose, and can solve the problems of heavy chemical synthesis workload and the like

Active Publication Date: 2019-02-05
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It has been reported in the literature that the workload of chemical synthesis is large, and it is mainly to modify and transform disaccharides that are similar in structure to epilactose

Method used

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  • Batch synthesis method of epilactose
  • Batch synthesis method of epilactose
  • Batch synthesis method of epilactose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Example 1. Batch synthesis of epilactose

[0102] according to figure 1 The shown synthesis route is used to synthesize epilactose in batches, and the specific steps are as follows:

[0103] (1) Synthesis of compound represented by formula IV:

[0104]

[0105] Compound II (20g, 0.074mol), p-toluenesulfonic acid (7g, 0.037mol) and magneton were added to a 200ml round bottom flask. Add 100ml dry DMF and 2-methoxypropene (7.27ml, 0.078mol) under nitrogen protection, and react at room temperature (25°C) for 2 hours. TLC[V(Petroleum Ether) / V(Ethyl acetate)=1:2] detected that the reaction was complete, and it was allowed to react overnight (ie 12 hours) in an oil bath at 70°C. TLC[V(petroleum ether) / V(ethyl acetate)=1:2] detected that the reaction was complete, and added 10ml of triethylamine to stop the reaction. Under reduced pressure distillation, 30 mL×3 toluene was used to co-evaporate DMF to obtain a crude product. It was recrystallized with V (petroleum ether):V (ethyl a...

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Abstract

The invention discloses a batch synthesis method for 4-O-beta-Galactopyranosyl-D-mannopyranoside. The batch synthesis method of 4-O-beta-Galactopyranosyl-D-mannopyranoside comprises the steps of 1) conducting the isopropylidenation of the compound shown in formula II with 2, 3-hydroxy to obtain the compound shown in formula IV; 2) protecting the 6-hydroxy of the compound shown in formula IV through an acylation reaction to obtain the compound shown in formula V; 3) carrying out a coupling reaction between the compound shown in formula V and the compound shown in formula III to obtain the compound shown in formula VI; 4) removing the isopropylidene protection, benzyl protection, R1 protection and R2 protection of the compound shown in formula VI to obtain the compound shown in formula I. The alpha-D-benzyl mannoside (formula II) serves as a starting material, glycosyl acceptor 2, 3-O-isopropylidene-6-O-benzoyl-alpha-D-pyran benzyl mannoside (formula V) intermediate is obtained through a two-steps reaction, the yield and purity in each step of the reaction are very high, accordingly, in a large-scale preparation, the intermediates IV and V do not require purification and can be directly used in the next step of the reaction.

Description

Technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a batch synthesis method of epilactose. Background technique [0002] Epilactose is an isomer of lactose, and its chemical structure is galactose-(β-1→4)-mannose. Epilactose is a rare disaccharide, and a very small amount exists in the heat-treated milk. As a reducing disaccharide, epilactose has good probiotic effects. For example, epilactose can make a variety of bifidobacteria proliferate in the epilactose liquid. Bifidobacterium is a class of strictly anaerobic Gram-positive bacteria, which is an important probiotic that promotes the health of humans or animals. Bifidobacterium can also prevent and treat rotavirus infection, allergic diseases and inflammatory bowel disease. At the same time, epilactose can also promote the absorption of minerals in the intestine. Because epilactose is a non-digestible sugar, it can be fermented by intestinal microorganisms to produ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H3/04C07H9/04C07H15/18
CPCY02P20/55
Inventor 张建军王家尧梁晓梅王道全
Owner CHINA AGRI UNIV
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