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Glycosyl donor and application of glycosyl donor in preparation of glucoside

A donor and sugar-based technology, applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of insufficient mild conditions and poor functional group compatibility

Pending Publication Date: 2022-02-22
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are many methods for constructing glycoside compounds, but the conditions of these methods are not mild enough and the functional group compatibility is poor.
At the same time, most of the existing methods are difficult to prepare glycoside compounds with high stereoselectivity

Method used

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  • Glycosyl donor and application of glycosyl donor in preparation of glucoside
  • Glycosyl donor and application of glycosyl donor in preparation of glucoside
  • Glycosyl donor and application of glycosyl donor in preparation of glucoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] The synthesis of embodiment 1, compound 3

[0093] According to the following synthetic route 1, compound 3 was obtained.

[0094]

[0095] Reaction condition 1:

[0096] Under nitrogen protection, Box ligand (0.1 equiv.) and catalyst (0.05 equiv.) were added to the reaction flask, and then triethylamine (3.0 equiv.) and dry toluene solvent were added. Under nitrogen protection, stir at 80°C for 15 minutes. Then cooled to room temperature, under the protection of nitrogen, the whole Ac-protected mercaptoglucose substrate 1 (1.0 equiv) and periodiodine reagent 2 (1.5 equiv.) were sequentially added and reacted under the protection of nitrogen.

[0097] Reaction condition 2:

[0098] Add all Ac-protected mercaptoglucose substrate 1 (1.0 equiv.) and periodine reagent 2 (1.5 equiv.) into a round bottom flask, add dry toluene, Cu catalyst (0.2 equiv.), and triethyl Amine (3.0 equiv.), heated reaction under nitrogen protection. After the reaction was completed, diatom...

Embodiment 2

[0104] The synthesis of embodiment 2, compound 4

[0105]

[0106] (3R,4R,5S,6S)-2-((2'-iodo-[1,1'-biphenyl]-2-yl)thio)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate

[0107] 1 H NMR (400MHz, CDCl 3 )δ: 7.94 (dd, J = 8.0, 1.3Hz, 1H), 7.69 (dd, J = 7.7, 1.5Hz, 0.5H), 7.62 (dd, J = 7.6, 1.5Hz, 0.5H), 7.45–7.30 (m,3H),7.21(ddd,J=11.0,7.6,1.7Hz,1H),7.15(ddd,J=7.4,4.4,1.7Hz,1H),7.08(tt,J=7.7,1.9Hz,1H ),5.42(d,J=1.7Hz,0.5H),5.38(dd,J=2.9,1.7Hz,0.5H),5.34(d,J=1.7Hz,0.5H),5.24(dd,J=3.2 ,1.6Hz,0.5H),5.17–4.95(m,2H),4.23(dq,J=9.2,6.2Hz,0.5H),4.08–3.98(m,0.5H),2.13(d,J=2.7Hz ,3H),2.03(d,J=5.9Hz,3H),1.96(d,J=2.5Hz,3H),1.20(dd,J=6.2,3.3Hz,3H).

Embodiment 3

[0108] The synthesis of embodiment 3, compound 5

[0109]

[0110] (3S,4R,5R)-2-((2'-iodo-[1,1'-biphenyl]-2-yl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

[0111] 1 H NMR (400MHz, CDCl 3 )δ: 7.92(dd, J=7.9, 1.3Hz, 1H), 7.74(dd, J=7.1, 1.8Hz, 0.6H), 7.70–7.65(m, 0.4H), 7.43–7.31(m, 3H) ,7.22(ddd,J=7.7,6.1,1.7Hz,1H),7.18–7.12(m,1H),7.06(td,J=7.6,1.7Hz,1H),5.26(ddq,J=13.8,5.4, 2.5Hz, 1H), 5.18(t, J=8.3Hz, 0.6H), 5.10(t, J=7.6Hz, 0.4H), 5.01(ddd, J=10.7, 8.2, 3.4Hz, 1H), 4.82( d,J=8.0Hz,0.6H),4.72(d,J=7.1Hz,0.4H),4.08(ddd,J=14.2,12.6,4.5Hz,1H),3.63(ddd,J=17.5,12.6, 2.4Hz, 1H), 2.11(d, J=6.0Hz, 3H), 1.97(d, J=2.1Hz, 3H), 1.91(d, J=8.7Hz, 3H).

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Abstract

The invention discloses a glycosyl donor and application of the glycosyl donor in preparation of glucoside. Specifically provided is a glycosyl donor represented by formula I, or a salt thereof, or a stereoisomer thereof, or an optical isomer thereof. The glycosyl donor is novel in structure and simple in preparation method; the glycosyl provided by the invention is used as a raw material, glucoside (such as C-glycoside) with special alpha configuration can be prepared, and the preparation method is simple, mild in reaction condition and high in yield, and has a very good application prospect.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a glycosyl donor and its use in preparing glycosides. Background technique [0002] Carbohydrates are important components of organisms (including animals, plants, and microorganisms). Polysaccharides, oligosaccharides, and their glycocomplexes combined with proteins and esters are involved in cells, especially the entire time and space processes of multicellular life. They participate in various recognition processes of cells as information molecules: transmitting biological information, It participates in the immune regulation of the body and is closely related to cell differentiation, fertilization, embryonic development, blood system, infection, aging and many other functions. In recent years, due to the remarkable physiological activity of carbohydrates, chemists have attracted more and more research interests. Glycosides are an important form of sugar in natur...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00C07H13/04C07H15/18C07D309/10C07D487/04C07H21/04C07H17/04C07F9/655C07K5/062C07K5/083C07K9/00
CPCC07H15/203C07H1/00C07H13/04C07H15/18C07D309/10C07D487/04C07H21/04C07H17/04C07F9/6552C07K5/06026C07K5/0808C07K9/001C07B2200/07
Inventor 钮大文张霞尚卫东时荣
Owner SICHUAN UNIV
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