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Method for synthesizing D-mannoheptulose

A technology for mannoheptulose and mannoheptulose is applied in the field of synthesis of D-mannoheptulose, can solve the problems such as the complicated transformation method, and achieves the effects of low production cost, mild conditions and short process route

Inactive Publication Date: 2009-07-08
NANJING UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Martin O.R. et al. After increasing the carbon chain through the Wittig reaction, the functional group transformation of the α-hydroxy ketone structure was finally realized through multi-step reactions such as the oxidation of the double hydroxyl group of the olefin, the protection of the primary hydroxyl group, and the oxidation of the secondary hydroxyl group. The method of transformation is very cumbersome.

Method used

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  • Method for synthesizing D-mannoheptulose

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preparation example Construction

[0017] The invention discloses a synthetic method of D-mannoheptulose, comprising the following steps:

[0018] Step 1: Preparation of 3,4,5,6,7-penta-O-benzylmannoheptosene,

[0019] in N 2 Under protection, add anhydrous toluene to triphenylmethylphosphine bromide, add n-butyl lithium in n-hexane solution dropwise to the system under ice-cooling, heat up, then add 2,3 , 4,5,6-penta-O-benzylmannose, after the reaction, add acetone and water to terminate the reaction, extract, wash, dry, concentrate, and obtain 3,4,5,6,7-penta by silica gel column chromatography -O-Benzylmannoheptosene;

[0020] In the above process, the Wittig reagent made of triphenylmethylphosphine bromide and n-butyllithium needs to be in excess of 2,3,4,5,6-penta-O-benzylmannose, and the dosage of the two is relative to The amount of 2, 3, 4, 5, 6-penta-O-benzylmannose should not be less than 2 times the molar equivalent; when preparing Wittig reagent, the reaction should be carried out in an ice bath ...

Embodiment 1

[0029] In the 100mL there-necked flask, add 12.8g (35.7mmol) triphenylmethylphosphine bromide, N 2 Add 35mL of anhydrous toluene under protection and stir well. Under an ice bath, add 23 mL of 1.6 mol / L BuLi n-hexane solution dropwise, and heat up to 35°C after 40 min. At this time, the reaction system appears dark yellow. Add 6.4 g (10.2 mmol) of 2,3 dissolved in 10 mL of anhydrous toluene dropwise, 4,5,6-penta-O-benzylmannose, 28°C reaction 2d. 10 mL of acetone and 10 mL of water were added to stop the reaction. Concentrate, 80mL CH 2 Cl 2 Dissolved, washed with 3 × 200mL water successively, Na 2 SO 4 Drying, filtration, concentration, and silica gel column chromatography (V (ethyl acetate): V (petroleum ether) = 1: 8 elution) gave 5.8 g of light yellow syrupy 3,4,5,6,7-penta- O-benzylmannoheptosene (88% yield).

[0030] Add 4.54g (7.2mmol) 3,4,5,6,7-penta-O-benzylmannoheptosene to a 250mL round bottom flask, add 70.3mL acetone, 13.9mL water, 3.2mL acetic acid to diss...

Embodiment 2

[0033] Add 12.6g (35.3mmol) triphenylmethylphosphine bromide in 100mL there-necked flask, N 2 Add 40mL of anhydrous toluene under protection and stir well. Under an ice bath, add 33 mL of 1.2 mol / L BuLi n-hexane solution dropwise, and heat up to 25°C after 1 hour. At this time, the reaction system appears dark yellow. Add 8.0 g (12.7 mmol) of 2,3 dissolved in 10 mL of anhydrous toluene dropwise, 4,5,6-penta-O-benzylmannose, react at room temperature for 36h. 10 mL of acetone and 10 mL of water were added to stop the reaction. Concentrate, 80mLCH 2 Cl 2 Dissolved, washed with 3 × 200mL water successively, Na 2 SO 4 Drying, filtration, concentration, and silica gel column chromatography (V (ethyl acetate): V (petroleum ether) = 1: 8 elution) gave 6.7 g of light yellow syrupy 3,4,5,6,7-penta- O-Benzylmannoheptosene (82% yield).

[0034] Add 5.60g (8.9mmol) 3,4,5,6,7-penta-O-benzylmannoheptosene to a 250mL round bottom flask, add 86.3mL acetone, 13.9mL water, 4.2mL acetic a...

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Abstract

The invention discloses a method for synthesizing D-mannoheptulose, which comprises the following main steps that: step 1, penta-O-benzylmannose performs a Wittig reaction with methytriphenyl phosphonium bromide and n-butyl lithium, and a carbon chain is grown to obtain 3, 4, 5, 6, 7-penta-O-benzylmannose glucal; step 2, under a potassium permanganate system, the benzylmannose glucal is selectively oxidized into 3, 4, 5, 6, 7-penta-O-benzyl mannoheptose alpha-hydroxyl hemiketal; and step 3, palladium carbon is hydrogenated to remove a benzyl group, and is acid hydrolyzed to obtain the D-mannoheptulose. The invention provides new technical support for the preparation of seven-carbon rare sugar; and the method has the advantages of easily obtained raw materials, mild conditions, and simple preparation process, is easy to perform in laboratories and expected to realize the industrialization, and has relatively short process route and low production cost.

Description

technical field [0001] The invention relates to a synthesis method of D-mannoheptulose, especially a potassium permanganate system oxidized glucosene to prepare the α-hydroxy hemiketal structure of mannoheptulose, and finally debenzylated and acidified to synthesize D- Mannoheptulose method. Background technique [0002] D-mannoheptulose is a rare seven-carbon sugar extracted from the fruit of camphor pear (avocado). It has medicinal effects such as inhibiting hexokinase, inhibiting insulin secretion, treating obesity and anti-cancer. At the same time, it can also be used for the treatment and prevention of innate immune variant diseases. Due to its good biological activity, it has attracted the attention of organic synthetic chemistry, sugar chemistry and medical circles for more than half a century. [0003] In the early days, D-mannoheptulose was prepared by biological fermentation, and the scope of application was limited; by investigating the chemical synthesis report...

Claims

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Application Information

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IPC IPC(8): C07H7/02
Inventor 方志杰程杰王立成王光辉蔡亚李松陈凯张振宇
Owner NANJING UNIV OF SCI & TECH
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