C- aryl glycoside compound and synthesis method thereof

Abstract

The invention relates to a C-aryl glycoside compound and a synthesis method thereof. A structural formula of the compound is shown in the description, wherein R is H, acetyl, methyl formate group, NHBoc or 4-methoxy; basic reaction takes glycosyl bromide and aryl iodine (bromine) as a substrate, and reaction is gently performed for 6-12 hours under icy-water bath or normal temperature under actions of a catalyst, a ligand, a reducer and an additive, so that the C-aryl glycoside compound is obtained. The catalyst metal is relatively cheap, raw materials are simple and easily available, the reaction is moderate, one-step reaction is performed, steps are simple, operations are safe, and the yield is relatively high, so that stereoselectivity is relatively good.

Description

technical field [0001] The invention relates to a C-aryl glycoside compound and a synthesis method thereof. technical background [0002] At present, the synthesis methods of C-aryl glycosides mainly include: the C-glycosylation reaction of glycosyl halides, which undergoes glycosyl cations (Zeng, J.; Vedachalam, S.; Xiang, S.; Liu, The final product, the productive rate is higher, but the stereoselectivity of C-aryl glucoside compounds synthesized by this type of method is relatively poor, and the preparation of aryl nucleophile is also troublesome in addition; Next is 1,2-dehydrosugar and aromatic This method still needs to prepare organometallic reagents in advance, which is troublesome, and most of them can only provide furanoside compounds, but this method can well control the formation of α (Tatina, M.B.; Kusunuru, A.K.; Mukherjee , D.Org.Lett.2015,17,4624-4627.) or β (Mayato,C.; Dorta,R.L.; Vazquez,J.T.Tetrahedron:Asymmetry 2007,18,931-948.) configuration product ge...

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Problems solved by technology

[0002] At present, the synthesis methods of C-aryl glycosides mainly include: the C-glycosylation reaction of glycosyl halides, which undergoes glycosyl cations (Zeng, J.; Vedachalam, S.; Xiang, S.; Liu, The final product, the productive rate is higher, but the stereoselectivity of C-aryl glucoside compounds synthesized by this type of method is relatively poor, and the preparation of aryl nucleophile is also troublesome in addition; Next is 1,2-dehydrosugar and aromatic This method still needs to prepare organometallic reagents in advance, which is troublesome, and most of them can only provide furanoside compounds, but this method can well control the formation of α (Tatina, M.B.; Kusunuru, A.K.; Mukherjee , D.Org.Lett.2015,17,4624-4627.) or β(Mayato,C.; Dorta,R.L.; Vazquez,J.T.Tetrahedron:Asymmetry 2007,18,931-948.) configuration product generation; secondly, by Glycosyl metal (Sn, Se) reagents react with aryl electrophiles to generate C-aryl glycoside compounds, but the catalysts used in this method are relatively expensive, and the glycosyl metal reagents need to be prepared in advance, which is troublesome (J.Am. Chem.Soc.139,49,17908-17922); In addition, methods such as attacking sugar lactones by nucleophiles are also widely used, but there are still many steps, and problems such as the preparation of organic nucleophiles in advance

[0003] In summary, the existing methods for producing C-aryl glucosides have the problems of expensive catalysts, cumbersome steps, complicated operations, the need to prepare organic nucleophiles in advance, and poor selectivity to α or β configuration products.

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