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Alkyl galactoside receptor, preparation method and application thereof

A technology of heptaacetyllactoside and alkyl group is applied in the field of alkyl lactoside receptor and its preparation, which can solve the problems of complex oligosaccharide synthesis and the like

Inactive Publication Date: 2011-11-16
CHONGQING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the complex structure of the sugar itself, each monosaccharide has multiple hydroxyl groups, so there are multiple reaction sites, and the difference between each hydroxyl group is very small, which makes the synthesis of oligosaccharides very complicated.

Method used

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  • Alkyl galactoside receptor, preparation method and application thereof
  • Alkyl galactoside receptor, preparation method and application thereof
  • Alkyl galactoside receptor, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of Octyllactoside Acceptor 4

[0021] 1,2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-1,2,3,6-tetra-O-acetyl-D- Synthesis of glucopyranoside 2

[0022] In a 500ml pear-shaped bottle, add 60ml of pyridine (dried with calcium hydride), and under stirring at room temperature, sequentially add lactose 1 (18.0g, 0.050mol), 60ml of acetic anhydride (excess) or 40ml of acetyl chloride (excess), and stir at room temperature for reaction 12 After the reaction was completed, 200ml of ethyl acetate was added, followed by washing with saturated brine, 1:1 hydrochloric acid solution, saturated sodium bicarbonate solution, and saturated brine to neutrality, and then washing with anhydrous sodium sulfate dry. After filtration, the solvent was recovered from the filtrate under reduced pressure, and finally a colloidal solid 2 (32.91 g) was obtained with a yield of 97%.

[0023] 2. Octyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β- Synthesi...

Embodiment 2

[0035]Preparation of dodecyllactoside acceptor 6

[0036] 1. Dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl- Synthesis of β-D-glucopyranoside 5

[0037] In a 250ml pear-shaped bottle, add 2 (20.4g, 0.03mol) and dodecanol (5.6g, 0.03mol) in sequence, add a stirrer, vacuumize for half an hour, inject 150ml of dry dichloromethane, stir, drop Add 15ml of boron trifluoride ether solution, react at room temperature for 24 hours, add 150ml of dichloromethane, and wash with saturated sodium bicarbonate solution and brine successively until neutral. The solvent was recovered under reduced pressure, the sample was dissolved in dichloromethane and refined on a silica gel column. First, the dodecanol was washed out with petroleum ether / ethyl acetate (6 / 1), and then the dodecyl alcohol was washed out with petroleum ether / ethyl acetate (3 / 1). The eluent was used to recover raw material 2 (9.6g) to obtain product 5 (11.1g).

[0038] [α] D =-2.5° (c=1.0, CHCl...

Embodiment 3

[0049] Preparation of cetyl lactosyl acceptor 8

[0050] 1. Hexadecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl- Synthesis of β-D-glucopyranoside 7

[0051] In a 250ml pear-shaped bottle, add 2 (20.4g, 0.03mol) and cetyl alcohol (7.3g, 0.03mol) in sequence, add a stirrer, vacuumize for half an hour, inject 150ml of dry toluene, stir, and drop three Boron fluoride ether solution 15ml, react at room temperature for 24 hours, add toluene 150ml, wash with saturated sodium bicarbonate solution and brine successively until neutral. Recover the solvent under reduced pressure, dissolve the sample in dichloromethane and refine it on a silica gel column, first wash out the cetyl alcohol with petroleum ether / ethyl acetate (7 / 1), and then use petroleum ether / ethyl acetate (4 / 1) as The eluent was used to recover raw material 2 (9.3g) to obtain product 7 (12.8g).

[0052] [α] D =-4.5° (c=1.0, CHCl3);

[0053] 1 H NMR (400MHz, CDCl3): δ5.31 (dd, 1H, J = 1.0, ...

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PUM

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Abstract

The invention discloses an alkyl 2,3,4,6-tetra-O-acetyl-beta-D-pyran galactosyl-(1->4)-2,3-di-O-acetyl-beta-D-pyran heteroside and a preparation method thereof. The raw material lactose is completely acetylized to react with alcohol to obtain alkyl-O-hepta-acetyl galactoside, and 6-acetyl on glucose group is selectively deacetylated to obtain the target compound. The synthesizing method provided in the invention has the advantages of simple, convenient and fast operation, low cost and the like. The invention also discloses an application of alkyl galactoside receptor in fast synthesizing non-natural oligosaccharide having antitumor activity.

Description

technical field [0001] The present invention relates to an alkyllactoside acceptor for preparing complex oligosaccharides and its preparation method and application, specifically 2,3,4,6-tetra-O-acetyl-β-D-pyran Galactosyl-(1→4)-2,3-di-O-acetyl-β-D-glucopyranoside and its preparation method and use. Background technique [0002] Oligosaccharides have a variety of pharmacological activities and are important information substances in organisms. They participate in the processes of communication, recognition, and signal transmission between cells, and also play an important role in the interaction between pathogens and host cells. Due to the complex structure of the sugar itself, each monosaccharide has multiple hydroxyl groups, so there are multiple reaction sites, and the difference between each hydroxyl group is very small, which makes the synthesis of oligosaccharides very complicated. So far, the synthesis of oligosaccharides is much more difficult than the synthesis of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/04C07H1/00A61P35/00
Inventor 衡林森王敏
Owner CHONGQING UNIV OF POSTS & TELECOMM
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