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A method for preparing L-ribose by reducing ketose by catalytic hydrogenation

A ribose and catalyst technology, which is applied in the field of preparing L-ribose by reducing ketose by catalytic hydrogenation, can solve the problems of high reaction temperature, poor atom economy, low yield and the like

Active Publication Date: 2011-12-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The shortcoming of this method is generally to need higher reaction temperature, and yield is lower, and atom economy is poor [Acton, E.M.; Ryan, K.J.; Goodman, L., J.Am.Chem.Soc., 1964,86( 23), 5352-5354]
Although hydroreduction is a cleaner and easier-to-handle method, it has not been used in the synthesis of L-ribose so far

Method used

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  • A method for preparing L-ribose by reducing ketose by catalytic hydrogenation
  • A method for preparing L-ribose by reducing ketose by catalytic hydrogenation
  • A method for preparing L-ribose by reducing ketose by catalytic hydrogenation

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Effect test

Embodiment 1

[0033] Embodiment 1, preparation L-ribose

[0034] The mixed system of 5g Raney Ni (Raney nickel), 200mL methanol and 10g 3,4-O-propylidene-2-deoxy-2-oxo-β-L-arabinoside (compound 3) was dissolved in 30atm hydrogen React under pressure for 72 hours at a reaction temperature of 20-30°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 to contain 3,4-O-propylidene-β-L-arabinoside 2 (content 8%) and 3,4-O-propylidene-β-L-riboside 4 (content 92%) ). The conversion efficiency was 92%. "Transformation efficiency" in the present invention refers to the generated 3,4-O-propylidene-β-L-riboside 4 relative to the 3,4-O-propylidene-2-deoxy-2- Oxo-β-L-arabinoside 3 ratio.

[0035] The NMR characterization of the resulting reduction product 3,4-O-propylidene-β-L-riboside 4 is as follows: 1 H-NMR (300MHz, CDCl 3 ), δ (ppm), 4.64 (1H, d, J = 3.5Hz, H1), 4.38 (1H, dd, J = 6.7Hz, 3.9Hz, H3),...

Embodiment 2

[0038] A mixed system of 50mg Pd / C (10%), 20mL ethanol and 100mg 3,4-O-propylidene-2-deoxy-2-oxo-β-L-arabinoside (compound 3) was dissolved in 50atm hydrogen React under pressure for 48 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 found that it contained 3,4-O-propylidene-β-L-arabinoside 2 (content 9%), ketose 3 (content 85%) and 3,4-O-propylidene-β-L - Riboside 4 (content 6%). The conversion efficiency was 38%. 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, v / v) to obtain 3,4-O-propylidene- β-L-riboside 4.

[0039] The resulting reduction product 3,4-O-propylidene-β-L-riboside 4 was reacted at 90°C for 12 hours in the presence of a macroporous strongly acidic styrene-based cation exchange resin to obtai...

Embodiment 3

[0041] 50mg Pd(OH) 2 , 20mL of methanol and 100mg of 3,4-O-propylidene-2-deoxy-2-oxo-β-L-arabinoside 3 mixed system was reacted under 50atm hydrogen pressure for 72 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 3,4-O-propylidene-β-L-arabinoside 2 (content 11%), ketose 3 (content 67%) and 3,4-O-propylidene-β-L - Riboside 4 (content 22%). The conversion efficiency was 68%. 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, v / v) to obtain 3,4-O-propylidene- β-L-riboside 4.

[0042] The resulting reduction product 3,4-O-propylidene-β-L-riboside 4 was reacted at 90°C for 12 hours in the presence of a macroporous strongly acidic styrene-based cation exchange resin to obtain L-ribose, whic...

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Abstract

The invention discloses a method for preparing L-ribose by reducing ketose by a catalytic hydrogenation method. The method comprises the following steps of: 1) performing a reduction reaction on a compound shown in a formula III in the presence of a transition metal catalyst and hydrogen so as to obtain a compound shown in a formula IV, wherein R1 and R2 are protecting groups of dyhydroxyl, and R3 is an anomeric carbon glucoside protecting group; and 2) removing R1, R2 and R3 protecting groups from the compound shown in the formula IV so as to obtain the L-ribose shown in a formula I. The method has the advantages of high stereoselectivity, cleanliness, convenience in aftertreatment and the like, and is a preparation method which is suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for preparing L-ribose by reducing ketose by a catalytic hydrogenation method. Background technique [0002] L-ribose, the chiral enantiomer of D-ribose, does not exist in nature and organisms, and is a relatively expensive and rare sugar. L-ribose has good anti-tumor and anti-viral activities and has little toxic and side effects on normal cells. More importantly, L-ribose is a key intermediate in the synthesis of L-nucleosides and L-nucleic acids. L-nucleosides are enantiomers of naturally occurring D-nucleosides, and some L-configuration nucleoside derivatives have better antiviral activity than their D-configuration enantiomers [Beach, J.W.; Jeong, L.S.; Alves , A.J.; Pohl, D.; Kim, H.O.; Chang, C.N.; Doong, S.L.; Schinazi, R.F.; ; Shanmuganathan, K.; Alves, A.J.; Jeong, L.S.; Beach, J.W.; Schinazi, R.F.; Chang, C.N.; This has led to intense interest in the physical and biological properties of L-nucleosides [A...

Claims

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Application Information

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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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