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Batch synthesis method for 4-O-beta-Galactopyranosyl-D-mannopyranoside

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: 2017-01-11
CHINA AGRI UNIV
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  • 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 for 4-O-beta-Galactopyranosyl-D-mannopyranoside
  • Batch synthesis method for 4-O-beta-Galactopyranosyl-D-mannopyranoside
  • Batch synthesis method for 4-O-beta-Galactopyranosyl-D-mannopyranoside

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Embodiment 1

[0101] Embodiment 1, batch synthesis epilactose

[0102] according to figure 1 The synthetic route shown is the batch synthesis of epilactose, and the specific steps are as follows:

[0103] (1) Synthesis of compound shown in formula IV:

[0104]

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

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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 in particular 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 that exists in very small amounts in heat-treated milk. As a reducing disaccharide, epilactose has a good prebiotic effect. For example, epilactose can make a variety of bifidobacteria proliferate in epilactose solution. Bifidobacterium (Bifidobacterium) belongs to a class of strictly anaerobic Gram-positive bacteria, and is an important probiotic for promoting human or animal health. Bifidobacterium also prevents and treats rotavirus infection, allergic diseases and inflammatory bowel disease. At the same time, lactose can also promote the absorption of minerals in the intestine. Since epilactose is an indigestible sugar, it can be fermented by intestinal microorganism...

Claims

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Application Information

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