A kind of preparation method of L-lyxose

A technology of lyxose and 5-O-, which is applied in the field of L-lyxose preparation, can solve the problems of complex sources of raw materials and difficulty in realizing large-scale production, and achieve cheap and easy-to-obtain raw materials, easy operation and high purity of products Effect

Inactive Publication Date: 2011-12-21
XIAMEN UNIV
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Problems solved by technology

In these methods, it is obtained from relatively simple raw materials through multi-step protection and deprotection, oxidation removal of terminal C-C bonds, or the sources of raw materials are complex, and it is difficult to achieve large-scale production

Method used

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  • A kind of preparation method of L-lyxose
  • A kind of preparation method of L-lyxose

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Embodiment Construction

[0027] The following examples will further illustrate the present invention, but do not limit content of the present invention:

[0028] At 25°C, dissolve 10g of L-arabinose (66.7mmol) in 300mL of pyridine, add 18.5g of triphenylchloromethane in portions, the solution turns from white turbidity to yellow and clear, stir for 20h, and convert pyridine with 4M hydrochloric acid after the reaction is completed It is pyridine hydrochloride, extracted with dichloromethane, removed the solvent under reduced pressure, and purified by flash silica gel column chromatography to obtain 7.8 g of white foamy solid (2), yield: 41%, mp=169-171°C. 1 H-NMR (400MHz, CDCl 3 ,): δ3.21-3.24(m, 1H), 3.34-3.40(m, 1H), 3.63-3.69(m, 1H), 3.89-3.90(m, 1H), 4.09-4.12(m, 1H), [5.3(s), 5.2(d, J=4.3Hz), 1H total, mixture of two anomers], 7.2-7.3(m, 15H); 13 C-NMR (100MHz, CDCl 3 ): δ58.3, 63.8, 76.4, 80.1, 85.1, 96.1, 127.1, 127.4, 128.0, 128.2, 128.8, 143.0, 143.5, 149.1.

[0029] Take 3.92g (2) (10mmo...

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Abstract

The invention relates to a preparation method of L-lyxose and relates to a five-carbon sugar. The invention provides a preparation method of L-lyxose and the method has cheap and easily available raw materials, fewer reagents and simple process. The technical scheme of the preparation method uses L-arabinose as a raw material; L-arabinose is subjected to hydroxyl protection and is reduced into a sugar alcohol, then the molecular configuration is changed under Swern oxidation condition, and finally the product L-lyxose with mirror symmetry conversion is obtained. The method comprises the following steps: synthesizing 5-O-triphenylmethyl-L-arabinose (2); synthesizing 5-O-triphenylmethyl-L-arabitol (3); synthesizing 5-O-triphenylmethyl-1,2,3,4-tetraacetylarabitol (4); synthesizing L-arabitol-1,2,3,4-tetraacetate (5); synthesizing L-lyxose-2,3,4,5-tetraacetate (6); and synthesizing L-lyxose (7).

Description

technical field [0001] The invention relates to a five-carbon sugar, in particular to a preparation method of L-lyxose. Background technique [0002] According to the information of the International Rare Sugar Society, the currently known rare monosaccharides include: L-ribulose, L-xylose, L-lyxose, L-psicose, etc. The distribution of rare monosaccharides in nature is very rare, but because these monosaccharides have some special physical and chemical properties, they have gained widespread attention and popularity in the scientific and technological circles. As one of the rare five-carbon sugars, L-lyxose is mainly obtained by multi-step chemical synthesis in addition to biological enzyme catalysis. However, the current method for chemically synthesizing L-lyxose is cumbersome, or the sources of raw materials are complicated. Therefore, it is of great significance to find a route to synthesize the rare sugar L-lyxose from cheap and easy-to-obtain raw materials and simple ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/02C07H1/00
CPCY02P20/55
Inventor 陈庆镇赵苏艳詹庄平
Owner XIAMEN UNIV
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