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Method for synthesizing D-mannoheptulose

A technology of mannoheptulose and mannoheptulose, which is applied in the field of synthesis of D-mannoheptulose, can solve the problems of cumbersome transformation methods and achieve the effects of low production cost, mild conditions and short process route

Inactive Publication Date: 2011-05-25
NANJING UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
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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 method for synthesizing D-mannoheptulose, comprising the following steps:

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

[0019] in N 2 Under the protection, anhydrous toluene was added to triphenylmethyl phosphine bromide, under ice bath, the n-hexane solution of n-butyllithium was added dropwise to the system, the temperature was increased, and 2,3 dissolved in anhydrous toluene was added. , 4,5,6-penta-O-benzylmannose, add acetone and water to terminate the reaction after the reaction, extract, wash, dry, concentrate, silica gel column chromatography to obtain 3,4,5,6,7-penta -O-benzylmannohepsene;

[0020] In the above-mentioned process, the Wittig reagent made by triphenylmethyl phosphine bromide and n-butyllithium needs to be excessively higher than 2,3,4,5,6-penta-O-benzyl mannose, and the two dosages are relative to The dosage of 2,3,4,5,6-penta-O-benzylmannose is not less than 2 times the molar equivalent; wh...

Embodiment 1

[0029] In a 100mL there-necked flask, add 12.8g (35.7mmol) triphenylmethyl phosphine bromide, N 2 Add 35 mL of anhydrous toluene under protection and stir well. Under the ice bath, 23mL of 1.6mol / L BuLi n-hexane solution was added dropwise, and the temperature was increased to 35°C after 40min. At this time, the reaction system was dark yellow. 4,5,6-Penta-O-benzylmannose, reacted at 28°C for 2d. Add 10 mL of acetone and 10 mL of water to stop the reaction. Concentrated, 80mL CH 2 Cl 2 Dissolved, washed with 3×200mL water in turn, Na 2 SO 4 Drying, filtration, concentration, silica gel column chromatography (V (ethyl acetate): V (petroleum ether) = 1:8 elution) to obtain 5.8 g of pale yellow syrupy 3,4,5,6,7-penta- O-benzylmannoheptenene (88% yield).

[0030] Add 4.54g (7.2mmol) 3,4,5,6,7-penta-O-benzylmannoheptonene to a 250mL round-bottomed flask, add 70.3mL acetone, 13.9mL water, 3.2mL acetic acid to dissolve, ice bath Mix well. 23.0mL of acetone and 1.80g (11.4mmo...

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 method for synthesizing D-mannoheptulose, in particular to a potassium permanganate system oxidizing glycone to prepare the alpha-hydroxy hemiketal structure of mannose, and finally debenzylation and acidification to synthesize D- Mannoheptulose method. Background technique [0002] D-mannoheptulose (D-mannoheptulose) is a rare hepta sugar extracted from avocado fruit. It has medicinal effects such as inhibiting hexokinase, inhibiting insulin secretion, treating obesity and anti-cancer. It can also be used to treat and prevent innate immune variant diseases. Due to its good biological activity, it has been concerned by the organic synthetic chemistry, carbohydrate chemistry and medical circles for more than half a century. [0003] In the early days, D-mannoheptulose was prepared by biological fermentation, and its application range was limited; by investigating reports on the chemical synthesis of D-mannoheptulose and simi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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