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Orthocarbonate-protected rhamnose donor and preparation method and application thereof

A technology of orthocarbonate and rhamnose, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of cumbersome preparation steps, narrow application range, unstable donors, etc., and achieve simple preparation Efficient and stable effect

Active Publication Date: 2020-05-19
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all existing methods for constructing β-glycosidic bonds have various defects such as cumbersome preparation steps, low efficiency, narrow application range, and unstable donors.
[0003] However, orthocarbonate protection has only been used in the field of polymers, and has never been used as a protecting group, and there is a lack of related removal methods

Method used

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  • Orthocarbonate-protected rhamnose donor and preparation method and application thereof
  • Orthocarbonate-protected rhamnose donor and preparation method and application thereof
  • Orthocarbonate-protected rhamnose donor and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Preparation of orthocarbonate-protected rhamnose donor D1, whose structural formula is:

[0038]

[0039] The reaction equation is:

[0040]

[0041] Prepared by:

[0042] Under the protection of argon, add pyridine (10 μL, 0.144 mmol) and 2,2-dichlorobenzo[1,3]dioxolane in sequence in dichloromethane solvent dissolved with D1' (120mg, 0.03mmol) Alkene (5.5 μL, 0.036 mmol), the reaction was terminated after 3 hours. Then dilute to 50ml with ethyl acetate, then wash once with 1M aqueous hydrochloric acid (50ml), once with saturated aqueous sodium bicarbonate (50ml), twice with saturated aqueous sodium chloride (50ml), separate the organic phase, Dry over anhydrous sodium sulfate, filter, spin dry, and pass through a column (200-300 mesh). Ethyl acetate-petroleum ether (V 乙酸乙酯 :V 石油醚 =1:15) as the eluent, the product was obtained as a white solid (140 mg, 90%).

[0043] Compound Characterization: As figure 1 as shown, 1 H NMR (600MHz, CDCl 3 ): δ7...

Embodiment 2

[0045] Embodiment 2 prepares the β-connected disaccharide compound, and its structural formula is:

[0046]

[0047] Table 1 Glycosyl acceptors S1-S9

[0048]

[0049]

[0050] 1. The glycosyl donor D1-1 whose LG leaving group is bromine is respectively combined with the glycosyl ligand S1-S3, using tetrakis(3,5-bis(trifluoromethyl)phenyl)silver borate, tetrafluoride Silver borate, silver hexafluoroantimonate, silver perchlorate, silver hexafluorophosphate, silver tetrakis(2,3,4,5,6-pentafluorophenyl)borate and tetrakis(perfluoro-tert-butoxy) Compounds P1-P3 are prepared by activation of weakly interacting silver salts such as silver aluminate.

[0051] (1) Preparation of Compound P1

[0052]

[0053] Under the protection of argon, the glycosyl donor D1-1 (41.2mg, 80.40μmol), isopropanol (5.8mg, 96.49μmol) and the fresh Molecular sieves (100 mg) were dissolved in a mixed solvent of dichloromethane and diethyl ether (1 / 3), stirred for 15 minutes, then cooled to ...

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PUM

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Abstract

The invention belongs to the technical field of chemical synthesis, and relates to a rhamnose donor and a preparation method and application thereof. The structural formula of the rhamnose donor is shown in the specification, wherein R2 is acyl; and LG is a leaving group. The rhamnose donor has the beneficial effects that the prepared orthocarbonate-protected rhamnose donor is utilized, a rhamnosebeta glycosidic bond is efficiently constructed through change of sugar ring conformation and the remote participation effect of the acyl, and moreover, removal of orthocarbonate protection is realized.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a rhamnose donor and its preparation method and application. Background technique [0002] Rhamnose is a very important monosaccharide, which widely exists in various bacteria and pathogenic microorganisms in the form of α or β glycosidic bonds. In order to better study its structure-activity relationship and develop related sugar vaccines, it is necessary to Efficient synthesis requires efficient construction of α and β glycosidic linkages. The α-glycosidic bond can be prepared by simple adjacent groups, but the β-glycosidic bond is always a huge challenge due to the anomeric effect, the steric effect of the 2-position, the △2 effect and the deoxygenation of the 6-position. However, all existing methods for constructing β-glucosidic bonds have various defects such as cumbersome preparation steps, low efficiency, narrow application range, and unstable donors. [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H9/04C07H15/04C07H15/18C07H1/00
CPCC07H9/04C07H15/04C07H15/18C07H1/00Y02P20/55
Inventor 蔡峰张永亮蒋振宁
Owner SHANDONG UNIV