Tetraacetyl talose compound and preparation method thereof

Abstract

The invention belongs to the field of chemical synthesis, in particular relates to a preparation method for a tetraacetyl talose compound. The cheap and readily available per-O-acetyl galactose is taken as a raw material, and the method comprises the following steps of: reacting galactose in hot acetic anhydride in the presence of sodium acetate to obtain penta-O-acetyl-beta-D-galactopyranose; selectively removing acetyl of 2OH under the action of trifluoroacetic acid; protecting the 2OH by using sulfonyl; and finally, in a protonic solvent, performing simple and high-efficiency three-step reaction to obtain tetraacetyl talose with the structures 1 and 2 in high yield by taking water or nitrite as a reagent. The prepared tetraacetyl talose compound can be converted into talose or serve as a chiral raw material for synthesizing other compounds with excellent performance.

Description

technical field

[0001] The invention belongs to the field of chemical synthesis, and specifically relates to a tetraacetyltalose compound and a preparation method thereof. Background technique

[0002] Sugar compounds, amino acids, alkaloids and hydroxy acids are natural raw materials for the synthesis of chiral compounds, and are widely used in the total synthesis of many natural compounds and biologically active compounds with excellent performance, such as the synthesis of anticancer drugs, antiviral agents, and agricultural antibiotics It has become a hotspot in the research of organic synthetic chemistry and sugar chemistry. As an epimer of D-glucose, the four chiral centers of talose are S, S, S, R in sequence. Among them, the two chiral centers of 2OH and 4OH are opposite to those of glucose. D-talose and its derivatives can be used as chiral raw materials or chiral catalysts to synthesize other biologically active compounds. However, the content of talose in natur...

Examples

preparation example Construction

[0015] The preparation method of bicyclic alcohol glycoside compound of the present invention comprises the following steps:

[0016]

Embodiment 1

[0017] Embodiment 1, the synthesis of intermediate 3:

[0018] Mix D-galactose (18.0g, 100mmol), sodium acetate (9.0g, 110mmol), and 72ml of acetic acid, and control the temperature at about 120°C. After the reaction is completed, pour the reaction solution into 500ml of ice cubes, stir to precipitate a white solid, petroleum Ethyl ether acetate was recrystallized to obtain 36.5 g of a white solid with a yield of 93.6%.

Embodiment 2

[0019] Embodiment 2, the synthesis of intermediate 4:

[0020] Dissolve β-pentaacetylgalactopyranose (7.8g, 20mmol) in 90% trifluoroacetic acid aqueous solution, react at room temperature for 6.0h, evaporate the solvent after the reaction is completed, add isopropyl ether to precipitate a white solid, and recrystallize to obtain a white crystal 4.6 g, the yield was 66.0%. , to 1,3,4,6-tetra-acetylgalactopyranose.

technical field

[0001] The invention belongs to the field of chemical synthesis, and specifically relates to a tetraacetyltalose compound and a preparation method thereof. Background technique

[0002] Sugar compounds, amino acids, alkaloids and hydroxy acids are natural raw materials for the synthesis of chiral compounds, and are widely used in the total synthesis of many natural compounds and biologically active compounds with excellent performance, such as the synthesis of anticancer drugs, antiviral agents, and agricultural antibiotics It has become a hotspot in the research of organic synthetic chemistry and sugar chemistry. As an epimer of D-glucose, the four chiral centers of talose are S, S, S, R in sequence. Among them, the two chiral centers of 2OH and 4OH are opposite to those of glucose. D-talose and its derivatives can be used as chiral raw materials or chiral catalysts to synthesize other biologically active compounds. However, the content of talose in natur...

Examples

preparation example Construction

[0015] The preparation method of bicyclic alcohol glycoside compound of the present invention comprises the following steps:

[0016]

Embodiment 1

[0017] Embodiment 1, the synthesis of intermediate 3:

[0018] Mix D-galactose (18.0g, 100mmol), sodium acetate (9.0g, 110mmol), and 72ml of acetic acid, and control the temperature at about 120°C. After the reaction is completed, pour the reaction solution into 500ml of ice cubes, stir to precipitate a white solid, petroleum Ethyl ether acetate was recrystallized to obtain 36.5 g of a white solid with a yield of 93.6%.

Embodiment 2

[0019] Embodiment 2, the synthesis of intermediate 4:

[0020] Dissolve β-pentaacetylgalactopyranose (7.8g, 20mmol) in 90% trifluoroacetic acid aqueous solution, react at room temperature for 6.0h, evaporate the solvent after the reaction is completed, add isopropyl ether to precipitate a white solid, and recrystallize to obtain a white crystal 4.6 g, the yield was 66.0%. , to 1,3,4,6-tetra-acetylgalactopyranose.

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