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Method for synthesizing rare ketohexose and ketoheptose from sugar acid lactone

A technology for rare ketohexose and sugar acid lactone, which is applied in the field of preparing rare ketohexose and heptulose, can solve the problems of difficult separation, rare raw materials, lengthy routes, etc., and achieves reduction of process steps and single protective group. , the effect of simplifying the separation operation

Inactive Publication Date: 2010-09-01
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] However, because these sugars are rarely distributed in nature, it is difficult to meet people's needs through separation and extraction from natural products, so many chemists have devoted themselves to obtaining these rare ketoses through chemical synthesis, but these methods There are often disadvantages such as rare raw materials, lengthy routes, and time-consuming, mainly in the following two aspects:
[0004] First, the method is not universal. Early literature reports that when low-carbon erythrose or arabinose is used as a raw material to carry out nucleophilic addition of dihydroxyacetone or nitroglycerin to increase the carbon chain, due to the stereoselectivity of the addition Poor, resulting in more epimeric products and difficult separation
Later, it was reported that rare ketohexose was obtained through aldol condensation reaction, but starting from non-sugar substances, chiral centers need to be constructed, which requires high stereoselectivity
[0005] Second, the route is too lengthy, in which the conversion of functional groups

Method used

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  • Method for synthesizing rare ketohexose and ketoheptose from sugar acid lactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Step 1: Preparation of 3,4,5,7-tetra-O-benzyl-1-deoxyiodomannoheptulose:

[0032] Add 1.50 g (2.79 mmol) of 2,3,4,6-tetra-O-benzyl-mannolactone, 60 mL of anhydrous toluene, and 0.53 mL of diiodomethane (6.39 mmol) into a 100 mL three-necked flask and stir well. The system was placed in an ice bath at -78°C and cooled for 10 minutes. N 2 Under protection, 3.50 mL of a n-butyllithium solution in n-hexane (5.60 mmol) with a concentration of 1.6 mol / L was slowly added dropwise thereto, and after the addition was completed, the reaction was carried out at -78° C. for 1.5 hours. Then add 15ml of saturated NH to the three-neck flask 4 Cl solution and stirred for 10 minutes to terminate the reaction. It was extracted with 2×20 ml of dichloromethane, and the organic phases were combined, dried and concentrated to obtain a yellow syrupy liquid.

[0033] Step 2: Preparation of 3,4,5,7-tetra-O-benzyl-mannoheptulose:

[0034] Dissolve the obtained yellow syrup in a 100ml one-ne...

Embodiment 2

[0041] Step 1: Preparation of 3,4,5,7-tetra-O-benzyl-1-deoxyiodomannoheptulose:

[0042] Add 1.50 g (2.79 mmol) of 2,3,4,6-tetra-O-benzyl-mannolactone, 60 mL of anhydrous toluene, and 0.53 mL of diiodomethane (6.39 mmol) into a 100 mL three-necked flask and stir well. The system was placed in an ice bath at -70°C and cooled for 20 minutes. N 2 Under protection, 1.92 mL of a n-butyllithium solution in n-hexane (3.07 mmol) with a concentration of 1.6 mol / L was slowly added dropwise thereto, and reacted at -70° C. for 0.5 hours after the addition was completed. Then add 15ml of saturated NH to the three-neck flask 4 Cl solution and stirred for 10 minutes to terminate the reaction. It was extracted with 2×20 ml of dichloromethane, and the organic phases were combined, dried and concentrated to obtain a yellow syrupy liquid.

[0043] Step 2: Preparation of 3,4,5,7-tetra-O-benzyl-mannoheptulose:

[0044] Dissolve the obtained yellow syrup in a 100ml one-necked flask with 35ml o...

Embodiment 3

[0048] Step 1: Preparation of 3,4,5,7-tetra-O-benzyl-1-deoxyiodomannoheptulose:

[0049] Add 1.50 g (2.79 mmol) of 2,3,4,6-tetra-O-benzyl-mannolactone, 60 mL of anhydrous toluene, and 0.53 mL of diiodomethane (6.39 mmol) into a 100 mL three-necked flask and stir well. The system was placed in an ice bath at -65°C and cooled for 20 minutes. N 2 Under protection, 3.99 mL of a n-butyl lithium solution in n-hexane (6.39 mmol) with a concentration of 1.6 mol / L was slowly added dropwise thereto, and after the addition was completed, the reaction was carried out at -65° C. for 1.5 hours. Then add 15ml of saturated NH to the three-neck flask 4 Cl solution and stirred for 10 minutes to terminate the reaction. It was extracted with 2×20 ml of dichloromethane, and the organic phases were combined, dried and concentrated to obtain a yellow syrupy liquid.

[0050] Step 2: Preparation of 3,4,5,7-tetra-O-benzyl-mannoheptulose:

[0051] Dissolve the obtained yellow syrup in a 100ml one-n...

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Abstract

The invention discloses a method for synthesizing rare ketohexose and ketoheptose from a raw material of sugar acid lactone, which comprises the following steps of: firstly, reacting the hydroxyl-protected sugar acid lactone with diiodomethane under the action of n-butyl lithium to prolong a carbon chain so as to obtain 1-deoxy iodo-ketose; secondly, in an alkaline environment, performing a hydrolysis reaction to ensure that hydroxyl radicals substitute iodine atoms so as to obtain a ketose intermediate; and finally, performing de-protection on the intermediate to obtain the needed rare ketoses. The method provides a new technical support for preparing the rare ketoses, has easily-available raw materials and simple and convenient operation and processing, is easy to be performed in a laboratory, is expected to realize industrialization, and has a comparatively simple and short process route and a low production cost.

Description

technical field [0001] The invention relates to a method for preparing rare ketohexose and heptulose, in particular to a method for synthesizing rare ketohexose and heptulose from saccharactone. Background technique [0002] D-psicose; D-sorbose; D-mannoheptulose and other rare ketoses are a kind of natural products with high biological activity. They have the functions of inhibiting hexokinase, inhibiting insulin secretion, treating obesity, anti-cancer and As a new sweetener and other functions, it can also be used to treat and prevent innate immune mutation diseases. Due to its good biological activity, it has been attracting attention from synthetic chemistry, glycochemistry and biochemistry. [0003] However, since these sugars are rarely distributed in nature, it is difficult to meet people's needs through separation and extraction from natural products, so many chemists have devoted themselves to obtaining these rare ketoses through chemical synthesis, but these meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H7/02C07H1/00
Inventor 方志杰李松程杰胡丹丹
Owner NANJING UNIV OF SCI & TECH
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