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Unsaturated thioglycoside compound as well as selective synthesis method and application thereof

A synthetic method and compound technology, applied in chemical instruments and methods, organic chemistry, sugar derivatives, etc., can solve the problems of limited substrate compatibility, poor selective synthesis, harsh reaction conditions, etc., and achieve universal substrate compatibility Wide, easy to handle, to achieve the effect of post-modification

Pending Publication Date: 2021-11-16
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nowadays, scientists have designed a variety of methods for synthesizing glucosinolate molecules containing unsaturated bonds, but the existing preparation methods all have a common disadvantage, that is, using thiol or thiophenol as a sulfur source, under relatively harsh conditions, Poor selective synthesis of 2,3-double bond glucosinolates
In addition, due to the harsh reaction conditions, the compatibility of substrates is relatively limited
Although there have been many reports on the synthesis methods of this type of molecules, a good method has not been found, which can achieve high selectivity and diversity synthesis, and obtain novel 2,3-double bond glucosinolate compounds

Method used

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  • Unsaturated thioglycoside compound as well as selective synthesis method and application thereof
  • Unsaturated thioglycoside compound as well as selective synthesis method and application thereof
  • Unsaturated thioglycoside compound as well as selective synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Synthesis of compound 2a:

[0061]

[0062] In a 25mL reaction tube, add triacetylglucosene (0.1mmol, 1.0equiv.), 3-methoxyphenyl thiosulfate (0.15mmol, 1.5equiv.), dibenzonitrile palladium dichloride (5.0mol %), (R)-(+)-1,1'-binaphthyl-2,2'-bisdiphenylphosphine (12.5mol%), acetonitrile (0.7mL, 0.075mmol / mL), evacuated for nitrogen, in The reaction was carried out at 90° C. for 12 hours. After the reaction was completed, it was dried, filtered, concentrated, and separated by column chromatography (PE / EA=5 / 1) to obtain a colorless liquid 2a (28.2 mg, 80%), Rf=0.5 ( PE / EA=5 / 1). 1 H NMR (400MHz, CDCl 3 )δ7.14(d,J=8.2Hz,1H),7.09–7.04(m,2H),6.75(ddd,J=8.3,2.4,1.0Hz,1H),4.42–4.36(m,1H),4.18 (qd,J=12.1,4.3Hz,2H),3.76–3.71(m,3H),2.04(s,3H),2.00(s,3H). 13 C NMR (101MHz, CDCl 3 )δ170.9,170.3,159.8,136.0,129.7,128.5,127.7,123.7,117.2,113.2,83.6,77.3,77.03(s),76.7,67.3,65.1,63.0,55.3,21.0,20.8.IR(film,cm -1 ) 3055, 1649, 1180, 1130, 951, 896, 850, 746, 706. HRMS (EI) Calcd...

Embodiment 2

[0064] Synthesis of compound 2b:

[0065]

[0066] In a 25mL reaction tube, add triacetylglucosene (0.1mmol, 1.0equiv.), 4-methoxyphenyl thiosulfate (0.15mmol, 1.5equiv.), dibenzonitrile palladium dichloride (5.0mol %), (R)-(+)-1,1'-binaphthyl-2,2'-bisdiphenylphosphine (12.5mol%), acetonitrile (0.7mL, 0.075mmol / mL), evacuated for nitrogen, in The reaction was carried out at 90° C. for 12 hours. After the reaction was completed, it was dried, filtered, concentrated, and separated by column chromatography (PE / EA=5 / 1) to obtain a colorless liquid 2b (27.4 mg, 78%), Rf=0.5 ( PE / EA=5 / 1). 1 H NMR (400MHz, CDCl 3 )δ7.14(d,J=8.2Hz,1H),7.09–7.04(m,2H),6.75(ddd,J=8.3,2.4,1.0Hz,1H),4.42–4.36(m,1H),4.18 (qd,J=12.1,4.3Hz,2H),3.76–3.71(m,3H),2.04(s,3H),2.00(s,3H). 13 C NMR (101MHz, CDCl 3 )δ170.9,170.3,159.8,136.0,129.7,128.5,127.7,123.7,117.2,113.2,83.6,77.3,77.03(s),76.7,67.3,65.1,63.0,55.3,21.0,20.8.IR(film,cm -1 ) 3055, 1649, 1180, 1130, 951, 896, 850, 746, 706. HRMS (EI) Calcd...

Embodiment 3

[0068] Synthesis of compound 2c:

[0069]

[0070] In a 25mL reaction tube, add triacetylglucosene (0.1mmol, 1.0equiv.), 4-chlorophenyl thiosulfate (0.15mmol, 1.5equiv.), dibenzonitrile palladium dichloride (5.0mol%) , (R)-(+)-1,1'-binaphthyl-2,2'-bisdiphenylphosphine (12.5mol%), acetonitrile (0.7mL, 0.075mmol / mL), evacuated for nitrogen, at 90°C Under the conditions of reaction for 12 hours, after the reaction was completed, it was dried, filtered, concentrated, and separated by column chromatography (PE / EA=5 / 1) to obtain a colorless liquid 2c (22.3mg, 58%), Rf=0.5 (PE / EA=5 / 1) EA=5 / 1). 1 H NMR (400MHz, CDCl 3 )δ7.41(d,J=8.4Hz,2H),7.26–7.11(m,3H),6.01–5.90(m,1H),5.81(d,J=10.1Hz,1H),5.64(s,1H ),5.30(dd,J=9.5,1.7Hz,1H),4.41–4.32(m,1H),4.27–4.07(m,2H),2.04(s,3H),2.00(d,J=3.8Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ170.7, 170.3, 133.9, 133.2, 129.1, 128.2, 128.0, 83.7, 67.4, 65.1, 63.1, 21.0, 20.8. IR (film, cm -1 ) 3053, 1653, 1180, 1130, 896, 854, 819, 746, 706. HRMS (EI) C...

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Abstract

The invention discloses a synthesis method for selectively synthesizing an alpha-thioglycoside compound as shown in a formula (II) and a beta-thioglycoside compound as shown in a formula (III), which comprises the following steps: in a reaction solvent, by taking triacetyl glucose alkene as a reaction raw material and organic thiosulfates with different substituent groups as a sulfur source, under the action of a metal palladium salt and a ligand, selectively synthesizing an alpha-thioglycoside compound (II) and a beta-thioglycoside compound (III). The synthesis method provided by the invention has the advantages of easily available and cheap raw materials, simple reaction operation, mild reaction conditions, high yield and excellent functional group tolerance. According to the invention, synthesis and modification of some complex molecules are realized, and an efficient method for selectively constructing the thioglycoside compound containing the unsaturated bond is provided for research of pharmaceutical chemistry.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to an asymmetric polysulfide compound and its synthesis method and application. Background technique [0002] Glucosinolates are an important class of glycoside compounds that not only play unique roles in biological phenomena and pharmaceutical sciences, but also in synthetic chemistry as key precursors of other glycosides, glycans, and glycoconjugates. effect. As for glucosinolate molecules containing unsaturated bonds, due to their reaction sites and the application of synthetic products, the synthesis methods of such molecules have attracted everyone's attention. Nowadays, scientists have designed a variety of methods for synthesizing glucosinolate molecules containing unsaturated bonds, but the existing preparation methods all have a common disadvantage, that is, using thiol or thiophenol as a sulfur source, under relatively harsh con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/14C07H17/07C07H1/00
CPCC07H15/14C07H17/07C07H1/00
Inventor 姜雪峰赵岩
Owner EAST CHINA NORMAL UNIV
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