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A method for preparing d-allose by reducing ketose by catalytic hydrogenation

A kind of technology of allose and catalyst, applied in the field of preparing D-allose

Active Publication Date: 2011-12-07
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although hydroreduction is a cleaner and easier-to-handle method, it has not been used in the synthesis of D-allose so far

Method used

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  • A method for preparing d-allose by reducing ketose by catalytic hydrogenation
  • A method for preparing d-allose by reducing ketose by catalytic hydrogenation
  • A method for preparing d-allose by reducing ketose by catalytic hydrogenation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1, preparation D-allose

[0035] A mixed system containing 10g Raney Ni (Raney nickel), 200mL methanol and 10g 1,2:5,6-O-dipropylidene-3-deoxy-3-oxo-α-D-glucose 2 was dissolved in 30atm hydrogen React under pressure for 72 hours at a reaction temperature of 28-35°C. The catalyst was filtered off, and the filtrate was spin-dried to obtain a pale yellow oily liquid. The product has been 1 H NMR detection found that it contained 1,2:5,6-O-dipropylidene-α-D-glucose 1 (content 18%) and 1,2:5,6-O-dipropylidene-α-D-A Lulose 3 (content 82%). The conversion efficiency was 82%. The "transformation efficiency" in the present invention refers to the 1,2:5,6-O-dipropylidene-α-D-allose 3 produced relative to the 1,2:5,6-O- Ratio of bispropylidene-3-deoxy-3-oxo-α-D-glucose 2.

[0036] The NMR characterization of 1,2:5,6-O-dipropylidene-α-D-allose 3 is as follows: 1 H-NMR (300MHz, CDCl 3 ), δ (ppm), 5.82 (1H, d, J = 3.8Hz), 4.62 (1H, dd, J = 5.0Hz, 4.1Hz), 4.30 (1H, ...

Embodiment 2

[0038] Embodiment 2, preparation D-allose

[0039] A mixed system containing 10mg Pd / C (10%), 20mL ethanol and 100mg 1,2:5,6-O-dipropylidene-3-deoxy-3-oxo-α-D-glucose 2 was dissolved in 50atm hydrogen React under pressure for 72 hours, and the reaction temperature is 28-35°C. The catalyst was filtered off, and the filtrate was spin-dried to obtain a pale yellow oily liquid. The product has been 1 H NMR detection revealed that it contained unreacted ketose 2 (content 86%) and 1,2:5,6-O-dipropylidene-α-D-allose 3 (content 14%). The conversion efficiency was 100%. The product was recrystallized in a mixed solvent of ethyl acetate / petroleum ether, and then separated by column chromatography (mobile phase: ethyl acetate / petroleum ether=1 / 3) to obtain 1,2:5,6-O-bispropylidene -α-D-Allose 3.

[0040] The resulting reduction product 1,2: 5,6-O-dipropylidene-α-D-allose 3 was reacted at 90°C for 12 hours in the presence of an acidic resin in the presence of a macroporous strongly a...

Embodiment 3

[0041] Embodiment 3, preparation D-allose

[0042] 10mg contains Pd(OH) 2 , 10mL of methanol and 20mg of 1,2:5,6-O-dipropylidene-3-deoxy-3-oxo-α-D-glucose 2 was reacted under 50atm hydrogen pressure for 48 hours, and the reaction temperature was 30- 40°C. The catalyst was filtered off, and the filtrate was spin-dried to obtain a pale yellow oily liquid. The product has been 1 H NMR detection found that it contained 1,2:5,6-O-dipropylidene-α-D-glucose 1 (content 6%), unreacted ketose 2 (content 66%) and 1,2:5,6 -O-dipropylidene-α-D-allose 3 (content 28%). The conversion efficiency was 81%. The product was recrystallized in ethyl acetate / petroleum ether mixed solvent, and then separated by column chromatography (mobile phase: ethyl acetate / petroleum ether=1 / 3, v / v) to obtain 1,2:5,6-O - Dipropylidene-α-D-allose 3.

[0043] The resulting reduction product 1,2: 5,6-O-dipropylidene-α-D-allose 3 was reacted at 90°C for 12 hours in the presence of an acidic resin in the presen...

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Abstract

The invention discloses a method for preparing D-allose by reducing ketose by a catalytic hydrogenation process, which comprises the following steps: 1) subjecting the compound of formula (II) to reduction reaction in the presence of a transitional metal catalyst and hydrogen to obtain a compound of a formula III, wherein R1 and R2 are dihydroxyl protective groups; and 2) removing the R1 and R2 protective groups from the compound of the formula III to obtain D-allose. The method has the advantages of high stereoselectivity, high cleanness, convenience for post treatment and the like and is a preparation method suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing D-allose by reducing ketose by a catalytic hydrogenation method. Background technique [0002] The rare sugar D-allose has important applications in food, health care, medicine and other fields, and has become a research hotspot among rare sugars due to its wide range of physiological functions. D-allose itself has the effect of inhibiting the proliferation of cancer cells, which means that people will hope to develop new drugs without side effects [Sui, L.; Dong, Y.Y.; Watanabe, Y.; Yamaguchi, F.; Hatano, N. ; Tsukamoto, I.; Izumori, K.; Tokuda, M., Int. J. Oncol., 2005, 27, 4, 907-912]. The researchers believe that its special function of inhibiting the proliferation of cancer cells may be derived from the structural similarity between the allose molecule and D-glucose. D-allose has an important inhibitory effect on phyllodes neutrophils without other harmful side effects [US5620960], which means that...

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 俞初一李意羡贾月梅胡祥国
Owner INST OF CHEM CHINESE ACAD OF SCI
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