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Dicarboxy Boc-L drivative, its preparing method and use

A high-proline, double-hydroxyl technology, applied in organic chemistry and other fields, can solve the problems of not reaching the level of automation of peptide synthesis

Inactive Publication Date: 2007-11-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First of all, as far as synthesis technology is concerned, the current oligosaccharide synthesis is far from the automation level of peptide synthesis. Therefore, through the mature peptide synthesis technology, the oligosaccharide analog library——glycoamino acid Oligo library, an attractive option

Method used

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  • Dicarboxy Boc-L drivative, its preparing method and use
  • Dicarboxy Boc-L drivative, its preparing method and use
  • Dicarboxy Boc-L drivative, its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] Embodiment 1: the synthesis of sugar oxime (compound 2)

[0099]

[0100] 5-deoxy-5-azido-2,3-O-isopropylidene-D-ribofuranose (1) (4.0 g, 18.6 mmol) was dissolved in 20 ml of dichloromethane, and pyridine was added at room temperature ( 5.9 ml, 74.4 mmol), hydroxylamine hydrochloride (2.6 g, 37.2 mmol), reacted under stirring for 12 hours, TLC showed that the reaction was complete. Add 20 milliliters of water to the reaction system, separate the liquids, extract the aqueous phase with 20 milliliters of ethyl acetate three times, combine the organic phases, dry the organic phases with anhydrous sodium sulfate, filter after drying, concentrate the filtrate under reduced pressure and separate by column chromatography (eluent: petroleum ether: ethyl acetate = 4:1), and 4.2 g of the product sugar oxime (compound 2) was obtained. The product was a white solid with a yield of 98%.

[0101] R f =0.44 (petroleum ether: ethyl acetate=2:1).

[0102] Melting point: 91-92℃. ...

Embodiment 2

[0107] Embodiment 2: the synthesis of the sugar oxime (compound 3) of TBS protection

[0108]

[0109] (2) (4.2 g, 18.2 mmol) was dissolved in 20 ml of dichloromethane, tert-butyldimethylsilyl chloride (4.3 g, 28.7 mmol), pyridine (3.8 ml, 47.5 mmol) were added successively at room temperature mol), after reacting under stirring for 24 hours, TLC showed that the reaction was complete. Add 20 milliliters of water to reaction system, separate liquid, water phase is extracted 3 times with 20 milliliters of dichloromethanes, combine organic phase, filter after organic phase is dried with anhydrous sodium sulfate, after the filtrate is concentrated under reduced pressure, separate through column chromatography (washing Removal agent: petroleum ether: ethyl acetate = 8: 1), to obtain 5.1 g of the product TBS-protected sugar oxime (compound 3). The product was a colorless syrup with a yield of 81%.

[0110] R f =0.78 (petroleum ether: ethyl acetate=4:1); R f =0.78 (petroleum e...

Embodiment 3

[0115] Embodiment 3: the synthesis of mesylate sugar oxime (compound 4)

[0116]

[0117] (3) (5.0 g, 14.5 mmol) was dissolved in 30 ml of dichloromethane, methanesulfonyl chloride (1.7 ml, 29.5 mmol) was added under ice cooling, triethylamine (4.1 ml, 29.5 millimoles), the dropwise addition was complete, and TLC showed that the reaction was complete. Add 30 milliliters of ice-water to reaction system, separate liquid, water phase is extracted 3 times with 30 milliliters of dichloromethane, combine organic phase, filter after organic phase is dried with anhydrous sodium sulfate, after the filtrate is concentrated under reduced pressure, separate through column chromatography ( Eluent: petroleum ether: ethyl acetate = 6: 1), and 6.1 g of the product mesylate sugar oxime (compound 4) was obtained. The product was a yellow oil in 100% yield.

[0118] R f =0.51 (petroleum ether: ethyl acetate=4:1); 0.74 (dichloromethane: ethyl acetate=30:1).

[0119] IRv max (film): 2933, ...

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Abstract

This invention relates to a double hydroxy, high proline ramification and the preparation method and application. The invention utilize 5 - nitrine - 5 - deoxypentose chirality structure to prepare 5 - nitrine methyl - 3, 4 -double shield hydroxy nitrone, furthermore utilize addition reaction of nitrone and ester enol siloxane type nucleophilic reagent, to prepare double hydroxy high proline ramification. This invention has good regioselectivity, high stereoselectivity, be able to proceeding bulk preparation.

Description

technical field [0001] The invention relates to a dihydroxyhomoproline derivative, a preparation method and application thereof. Background technique [0002] Amino acids and sugars are the two main synthetic building blocks that generate the material diversity in nature. Amino acids (α, β, γ, ...) in proteins and peptides can generate secondary structures, which are the basis for forming the three-dimensional spatial structure of molecules. Sugar widely exists in nucleosides, glycoproteins and glycolipids, and cells use the interaction of these molecules to complete intracellular and extracellular information transmission. Many important pathological processes such as metastasis, infection, and inflammation are related to the mutual recognition of these molecules. The research on their mutual recognition has become a frontier topic in the fields of biology and medicine. [0003] Combining the structural features of amino acids and sugars, that is, a class of compounds tha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/09C07D207/50
Inventor 俞初一苏青云
Owner INST OF CHEM CHINESE ACAD OF SCI
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