CN106397509A - 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside - Google Patents

2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside Download PDF

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CN106397509A
CN106397509A CN201610793535.8A CN201610793535A CN106397509A CN 106397509 A CN106397509 A CN 106397509A CN 201610793535 A CN201610793535 A CN 201610793535A CN 106397509 A CN106397509 A CN 106397509A
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陈浩
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Ningbo University
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    • C07H17/02Heterocyclic radicals containing only nitrogen as ring hetero atoms
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Abstract

The invention relates to the field of chemical synthesis and particularly discloses synthesis of 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside and hydrolysate. Tetraacetylated fucose and 5-trifluoromethyl-2-mercaptopyridine are taken as starting materials, a PFIL (phosphoryl coordination functionalized ionic liquid)-containing mixed solvent is taken as a reaction medium, the Lewis acid is taken as a catalyst, 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside is prepared through glycosylation under microwave irradiation, and then 1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside is obtained through hydrolysis. The starting materials for preparing 1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside are relatively cheap, the synthesis means is simple and rapid, the functionalized ionic liquid can be reused, and the cost is reduced greatly.

Description

2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-α-L- rock algae Pyranoside
Technical field
The present invention relates to chemosynthesis technical field, more particularly, to 2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyrrole Piperidinyl) sulfydryl-alpha-L- rock algae pyranoside and hydrolyzate synthesis.
Background technology
Saccharide compound forms important living matter with protein, nucleic acid.With the development of modern science and technology, relevant sugar The research of compound also achieves very big development.Correlational study be further differentiated into carbohydrate chemistry, sugared materia medica, glycobiology, Sugar engineering, Tang Zuxuedeng branch field.Sugar is not only energy substance, prior closely related with life process.Sugar can As biological information molecule, participate in multiple processes such as Organism immunoregulation, cell differentiation, fetal development.Containing pyridine groups and Sulfur-containing compound, has biological activity, has pyridine structure and contain element sulphur in multi-medicament, pesticide.Design synthesis and Research and develop this kind of compound to have great importance and application prospect.
There is problems with traditional glucosides synthetic method (as Chinese patent 95118925.5,201010101523.7 etc.): The factor such as poor repeatability, stereo selectivity are poor, synthetic route is cumbersome, the prices of raw materials are more expensive or intermediate is unstable it is difficult to Meet the requirement of purity and scale market it is therefore desirable to research and develop new synthetic method.In glycosylation reaction, lewis Acid catalysiss are the methods being most frequently with, and reaction medium is generally molecule-type organic solvent.Space due to lewis' acid slaine Steric hindrance is little, it is difficult to sufficiently be regulated and controled to glycosylation stereo selectivity during catalysis is glycosylation.Therefore, in tradition Catalyst system and catalyzing in, in most cases, stereo selectivity is not satisfactory.Must be able to catalyst center spatial environmentss are adjusted Control, is possible to improve glycosylation stereo selectivity.On the other hand, green solvent ionic liquid developed in recent years, Through being used to substitute conventional molecular type organic solvent, in chemical reaction.Due to the polarity of reaction medium, from neutral or pole Property molecule-type become ion-type so that glycosylation reaction mechanism is more rich and varied, for optimize reaction condition provide more Selection.
Content of the invention
For problems of the prior art, the present invention provides a kind of compound, specially 2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside and the synthesis of hydrolyzate.
The specific technical scheme of the present invention is as follows:
2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside, has Structure shown in Formulas I:
1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside (5-F3MPT-AFU), there is formula Structure shown in II:
1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside can be used as a kind of new fucose Glycosides zymolyte.
The present invention also provides above-claimed cpd 1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranose The preparation method of glycosides, its synthetic technology route is as follows:
With four acetylation fucosees and 5- trifluoromethyl -2- mercaptopyridine as initiation material, with containing phosphinylidyne polymerization of olefin using catalyst work( It is reaction medium that ionic liquid can be changed, and with lewis' acid as catalyst, under microwave exposure, carries out glycosylation reaction and prepares 2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside, then obtain through hydrolysis 1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside.
Wherein, the mol ratio of raw material four acetylation fucose and 5- trifluoromethyl -2- mercaptopyridine is 1:1~5, preferably 1:1~3, further for 1:1.
Phosphinylidyne polymerization of olefin using catalyst functionalized ion liquid (PFIL) of the present invention is the quaternary ammonium salt (PFIL-1) of having structure, season In microcosmic salt (PFIL-2), pyridiniujm (PFIL-3), imidazole salts (PFIL-4), double phosphoryl functionalized imidazole (PFIL-5) one Plant or multiple mixture:
Wherein, R1, R2, R3, R4=hydrogen, alkyl, alkoxyl, aryl;N=1,2,3,4,5,6;X=(CF3SO2) N, PF6.
Preferably, R1, R2, R3, R4For hydrogen, methyl, ethyl, propyl group, butyl, amyl group, hexyl, alkoxyl, phenyl.
As one kind preferred embodiment, ion liquid of quaternaries (PFIL-1), preferably R in the present invention1、R2=second Epoxide, phenyl;R3=ethyl, propyl group, butyl.Its preparation method is as follows, by triethylamine, tripropyl amine (TPA), tri-n-butylamine or triamylamine with Bromo alkyl diphenyl phosphine oxide or bromo alkyl ethoxy phenyl phosphine oxide are 1: 1~1.2 mixing in molar ratio, add organic Solvent, is positioned in microwave reaction device, is 350W~500W in microwave power, and reaction temperature is 80 DEG C~110 DEG C, during reaction Between for stirring reaction under conditions of 60min~150min, obtain crude product, remove unreacting material, obtain quaternary ammonium bromide ion Liquid.By the bis trifluoromethyl imine lithium of the quaternary ammonium obtaining bromide ionic liquid and equimolar amountss or hexafluorophosphoric acid nak response, obtain To described ion liquid of quaternaries (PFIL-1), structure is as shown in formula III.
Quaternary phosphonium salt ionic liquid (PFIL-2), preferably R in the present invention1、R2=ethyoxyl, phenyl;R3=phenyl.Its system Preparation Method is as follows:By triphenylphosphine and bromo alkyl diphenyl phosphine oxide, bromo alkyl phenyl-phosphonic acid ethyl ester or bromo alkylphosphines Diethyl phthalate is 1: 1~1.2 mixing in molar ratio, adds organic solvent, is positioned in microwave reaction device, in microwave power is 350W~500W, reaction temperature is 80 DEG C~110 DEG C, and the response time is stirring reaction under conditions of 60min~150min, obtains Crude product, removes unreacting material, obtains quaternary phosphonium bromide ionic liquid.By the quaternary phosphonium obtaining bromide ionic liquid and equimolar amountss Bis trifluoromethyl imine lithium or hexafluorophosphoric acid nak response, obtain described quaternary phosphonium salt ionic liquid (PFIL-2), structure such as formula Shown in IV.
Pyridine salt ionic liquid (PFIL-3), preferably R in the present invention1、R2=ethyoxyl, phenyl.Its preparation method is such as Under, by pyridine compounds and their and bromo alkyl diphenyl phosphine oxide, bromo alkyl phenyl-phosphonic acid ethyl ester or bromo alkyl phosphonic acid two Ethyl ester is 1: 1~1.2 mixing in molar ratio, adds organic solvent, is positioned over stirring reaction in microwave reaction device, microwave power For 350W~500W, reaction temperature is 80 DEG C~110 DEG C, and the response time is 60min~150min, obtains crude product, removes not Reaction raw materials, obtain pyridinium tribromide ionic liquid.Bis trifluoromethyl by the pyridinium tribromide obtaining ionic liquid and equimolar amountss Imine lithium or hexafluorophosphoric acid nak response, obtain described pyridine salt ionic liquid (PFIL-3), structure is shown as a formula V.
Imidazolium ionic liquid (PFIL-4), preferably R in the present invention1=methyl, ethyl, propyl group, butyl, amyl group, hexyl; R2=hydrogen;R3、R4=ethyoxyl, phenyl.Its preparation method is as follows:By glyoxaline compound and bromo alkyl diphenyl phosphine oxide, Bromo alkyl phenyl-phosphonic acid ethyl ester or bromo alkyl diethyl phosphonate are 1: 1~1.2 mixing in molar ratio, are positioned over microwave reaction In device, it is 280W~500W in microwave power, reaction temperature is 80 DEG C~120 DEG C, the response time is 60min~150min, Obtain crude product, remove unreacting material, obtain imidazoles bromide ionic liquid.By the imidazoles obtaining bromide ionic liquid with etc. rub The bis trifluoromethyl imine lithium of your amount or hexafluorophosphoric acid nak response, obtain described imidazole salt ionic liquid (PFIL-4), structure As shown in Formula IV.
Double phosphoryls functionalized imidazole ionic liquid (PFIL-5), preferably R in the present invention1、R2=ethyoxyl, phenyl.'s Preparation method is as follows:By imidazoles and bromo alkyl diphenyl phosphine oxide, bromo alkyl phenyl-phosphonic acid ethyl ester or bromo alkyl phosphonic acid Diethylester is with 1:2~4 mol ratio is dissolved in organic solvent, adds water soluble carbonate, is then placed into microwave reaction dress Carry out microwave reaction, microwave power is 280~500W, reaction temperature is 80~110 DEG C, the response time is 5~40min in putting, Obtain crude product after reaction, remove unreacted raw material, add anion exchanger in the crude product, carry out anion exchange, Obtain described double phosphoryls functionalized imidazole ionic liquid (PFIL-5), structure is as shown in Formula VII.
Described lewis' acid includes nickel salt, mantoquita, iron salt, pink salt, or scandium, yttrium, lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, Dysprosium, holmium, erbium, ytterbium, the salt of lutecium.
Described salt includes villaumite, sulfate, nitrate, fluoroform sulphonate or hexafluorophosphate.
For example, in the present invention, lewis' acid is ferric chloride, butter of tin, Ytterbium(III) nitrate., trifluoromethanesulfonic acid neodymium etc..
Catalytic reaction of the present invention is carried out under microwave-assisted.Can be timely according to the power of the degree adjustment microwave of reaction Between.In the present invention, microwave power is preferably 200~700W, further for 300~600W, further for 350~ 500W.In a preferred embodiment of the present invention, using intermittent type microwave irradiation, i.e. irradiation 3~10min, rests 0.5~2min Circulation irradiation.It is preferably irradiation 4~8min, rest 1~1.5min.Catalytic temperature is 35 DEG C~90 DEG C, preferably 40 DEG C~ 60 DEG C, further for 45 DEG C~55 DEG C.
In the above-mentioned catalytic reaction of the present invention, in reaction medium, also include alkyl chloride, that is, with phosphinylidyne polymerization of olefin using catalyst functionalization The mixed solvent of ionic liquid and chloralkane is as reaction medium.Wherein, chloralkane is dichloromethane, chloroform and 1, The mixture of one or more of 2- dichloroethanes.The present invention does not limit phosphinylidyne polymerization of olefin using catalyst functionalized ion liquid and alkyl chloride The usage ratio of hydrocarbon, using the arbitrary proportion containing phosphinylidyne polymerization of olefin using catalyst functionalized ion liquid all protection scope of the present invention it Interior.Preferably phosphinylidyne polymerization of olefin using catalyst functionalized ion liquid and the volume ratio of chloralkane are 0.2~0.8:10~20, further for 0.3~0.7:13~18, further for 0.5:15.
In the above-mentioned catalytic reaction of the present invention, also include general ionic liquid in reaction medium, that is, with phosphinylidyne polymerization of olefin using catalyst The mixed solvent of the general ionic liquid in functionalized ion liquid and this area is as reaction medium.Wherein general ionic liquid For commercial goods dialkylimidazolium salt, the alkyl of described dialkylimidazolium salt is methyl, ethyl, propyl group, butyl, amyl group, oneself Base, the anion of described dialkylimidazolium salt is bis trifluoromethyl imines ion, or hexafluorophosphate ion.The present invention does not limit phosphorus Acyl group is coordinated the usage ratio of functionalized ion liquid and general ionic liquid, using containing phosphinylidyne polymerization of olefin using catalyst functionalization ionic liquid The arbitrary proportion of body is all within protection scope of the present invention.Preferably phosphinylidyne polymerization of olefin using catalyst functionalized ion liquid and conventional ion liquid The volume ratio of body is 1:1~20, further for 1:4~10, further for 1:5.
Catalytic reaction obtains 2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyrrole Mutter after glucosides, 2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside is preferred In the methanol containing Feldalat NM, hydrolysis obtains 1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside. 1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside preparing can be used for preparing as substrate Fucosidase diagnostic reagent.
Beneficial effects of the present invention are as follows:
(1), using coordination functionalized ion liquid, and lewis' acid catalyst metals center complexation, by changing for the present invention Functionalized ion liquid structure, to regulate and control the sterically hindered size of metal ion center, thus changing the solid of glycosylation reaction Selectivity;
(2) microwave heating reaction be material in electromagnetic field because dielectric loss produces heat effect, have heating response fast, The features such as simultaneously heat inside and outside material.And ionic liquid has very high polarizability, it is a kind of good microwave absorbing material.By same When using microwave heating technique and ion liquid medium, accelerate firing rate, make reaction evenly, efficiency high.
(3) functionalized ion liquid used by is both as reaction medium, and as metal-ion ligand, has two kinds of functions concurrently.
1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside preparation method of the present invention rise Beginning raw material is relatively cheap, and synthesizing mean is simple, quick.2,3,4- triacetyl -1- (5- trifluoromethyl -2- the pyridine of the present invention Base) sulfydryl-alpha-L- rock algae pyranoside functionalized ion liquid used in preparation process can reuse, and enter one Step reduces cost.Rock is prepared as substrate using 1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside The cost of algae glycosidase diagnostic reagent is low, is conducive to effective popularization of fucosidase diagnostic reagent to use.
Specific embodiment
Below in conjunction with the embodiment in the present invention, the technical scheme in the embodiment of the present invention is carried out clearly and completely Description is it is clear that described embodiment is only a part of embodiment of the present invention, rather than whole embodiments.Based on this Embodiment in bright, the every other reality that those of ordinary skill in the art are obtained under the premise of not making creative work Apply example, broadly fall into the scope of protection of the invention.
In following examples, for convenience's sake, by 2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) mercapto Base-alpha-L- rock algae pyranoside is designated as glucosides 1,1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyrans Glucosides is designated as glucosides 2.
Embodiment 1:2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranose The preparation of glycosides
Weigh 0.486 gram of FeCl respectively3, four 0.33 gram of acetylation fucosees, 5- trifluoromethyl -2- mercaptopyridine 0.179 Gram, in parallel reaction pipe.It is separately added into 10mL dichloromethane, ionic liquid PFIL-1 [R under blanket of nitrogen1,R2,R3=ethyl, n =3, X=(CF3SO2)2N] 0.5mL, confined reaction test tube, stirring reaction, microwave exposure adopts batch (-type), power 350W, every time Irradiation 5 minutes, stops irradiating 1 minute.Reaction 5 hours, temperature control is in 40 degrees centigrade.It is anti-that reaction finishes the termination that adds water Should.Through silica gel chromatography post separation, obtain 0.29 gram of glucosides 1, yield 65%.Ionic liquid is reusable, and yield no substantially becomes Change.
Embodiment 2:2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranose The preparation of glycosides
Four 0.33 gram of acetylation fucosees, 0.179 gram of 5- trifluoromethyl -2- mercaptopyridine, in parallel reaction pipe.Nitrogen It is separately added into 10mL chloroform, ionic liquid PFIL-3 [R under atmosphere1,R2=phenyl, n=3, X=(CF3SO2)2N] 1mL and The anhydrous SnCl of 0.345mL4, confined reaction test tube, stirring reaction, microwave exposure adopts batch (-type), power 400W, each irradiation 5 Minute, stop irradiating 1 minute.Reaction 3 hours, temperature control is in 60 degrees centigrade.Reaction finishes the terminating reaction that adds water.Through silicon Glue chromatograph post separation, obtains 0.33 gram of glucosides 1, yield 73%.Ionic liquid is reusable, yield no significant change.
Embodiment 3:2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranose The preparation of glycosides
Weigh 0.591 gram of Nd (OTf) respectively3, four 0.33 gram of acetylation fucosees, 5- trifluoromethyl -2- mercaptopyridine 0.179 gram, in parallel reaction pipe.It is separately added into 10mL1,2- dichloroethanes, ionic liquid PFIL-2 [R under blanket of nitrogen1,R2, R3=phenyl, n=4, X=(CF3SO2)2N] 0.5mL, confined reaction test tube, stirring reaction, microwave exposure adopts batch (-type), work( Rate 500W, each irradiation 5 minutes, stop irradiating 1 minute.Reaction 5 hours, temperature control is in 80 degrees centigrade.Reaction finishes Add water terminating reaction.Through silica gel chromatography post separation, obtain 0.31 gram of glucosides 1, yield 70%.Ionic liquid is reusable, receives Rate no significant change.
Embodiment 4:2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranose The preparation of glycosides
Weigh 0.391 gram of Yb (NO respectively3)3, four 0.33 gram of acetylation fucosees, 5- trifluoromethyl -2- mercaptopyridine 0.179 gram, in parallel reaction pipe.Ionic liquid PFIL-4 [R is added under blanket of nitrogen1=propyl group, R2=hydrogen, R3、R4=ethoxy Base, n=5, X=PF6] 3mL, confined reaction test tube, stirring reaction, microwave exposure adopts batch (-type), power 500W, each irradiation 5 minutes, stop irradiating 1 minute.Reaction 5 hours, temperature control is in 40 degrees centigrade.Reaction finishes the terminating reaction that adds water.Warp Silica gel chromatography post separation, obtains 0.26 gram of glucosides 1, yield 58%.Ionic liquid is reusable, yield no significant change.
Embodiment 5:2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranose The preparation of glycosides
Weigh 0.30 gram of ScCl respectively3, four 0.33 gram of acetylation fucosees, 5- trifluoromethyl -2- mercaptopyridine 0.179 Gram, in parallel reaction pipe.Ionic liquid PFIL-5 [R is added under blanket of nitrogen1、R2=ethyoxyl, n=3, X=(CF3SO2)2N] 3mL, confined reaction test tube, stirring reaction, microwave exposure adopts batch (-type), power 350W, each irradiation 5 minutes, stops irradiation 1 Minute.Reaction 5 hours, temperature control is in 40 degrees centigrade.Reaction finishes the terminating reaction that adds water.Through silica gel chromatography post separation, Obtain 0.27 gram of glucosides 1, yield 60%.Ionic liquid is reusable, yield no significant change.
Embodiment 6:2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranose The preparation of glycosides
Weigh 0.30 gram of ScCl respectively3, four 0.33 gram of acetylation fucosees, 5- trifluoromethyl -2- mercapto-pyridine 0.179 Gram, in parallel reaction pipe.Ionic liquid PFIL-5 [R is added under blanket of nitrogen1、R2=ethyoxyl, n=3, X=(CF3SO2)2N] 2mL and general ionic liquid 3- butyl -1- Methylimidazole. hexafluorophosphate 2mL, confined reaction test tube, stirring reaction, microwave spoke According to adopting batch (-type), power 350W, each irradiation 5 minutes, stop irradiating 1 minute.Reaction 5 hours, temperature control is Celsius 40 About degree.Reaction finishes the terminating reaction that adds water.Through silica gel chromatography post separation, obtain 0.28 gram of glucosides 1, yield 62%.Ionic liquid Body is reusable, yield no significant change.
Embodiment 7:The preparation of 1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside
Take 0.90 gram of glucosides 1, be added in the 20mL methanol containing 0.1 gram of Feldalat NM, after reaction being stirred at room temperature 1 hour, Stopped reaction.After separating through silica gel column chromatography, obtain 0.5 gram of glucosides 2 compound, yield 83%.Mass spectrum (positive ion mode):m/ z 326.07(M+H)+.
It can be professional and technical personnel in the field's realization or use that above-mentioned embodiment is intended to illustrate the present invention, to above-mentioned Embodiment is modified and be will be apparent from for those skilled in the art, therefore the present invention includes but is not limited to Above-mentioned embodiment, any meet the claims or description description, meet with principles disclosed herein and novelty, The method of inventive features, technique, product, each fall within protection scope of the present invention.

Claims (10)

1.2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside, has Formulas I Shown structure:
2.1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside, has structure shown in Formula II:
3. 2,3,4- triacetyl -1- described in claim 1 (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyrrole Mutter glucosides preparation method it is characterised in that being initial former with four acetylation fucosees and 5- trifluoromethyl -2- mercaptopyridine Material, with containing phosphinylidyne polymerization of olefin using catalyst functionalized ion liquid as reaction medium, with lewis' acid as catalyst, under microwave exposure, Carry out glycosylation reaction and prepare 2,3,4- triacetyl -1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae Pyranoside.
4. method according to claim 3 is it is characterised in that described phosphinylidyne polymerization of olefin using catalyst functionalized ion liquid is to have formula The ion liquid of quaternaries of structure shown in III, there is the quaternary phosphonium salt ionic liquid of structure shown in formula IV, have shown in Formula V The pyridine salt ionic liquid of structure, there is the imidazole salt ionic liquid of structure shown in Formula IV and there is structure shown in Formula VII One or more of double phosphoryl functionalized imidazoles mixture:
Wherein, R1, R2, R3, R4=hydrogen, alkyl, alkoxyl, aryl;N=1,2,3,4,5,6;X=(CF3SO2) N, PF6.
5. method according to claim 4 is it is characterised in that the R of described phosphinylidyne polymerization of olefin using catalyst functionalized ion liquid1, R2, R3, R4For hydrogen, methyl, ethyl, propyl group, butyl, amyl group, hexyl, alkoxyl, phenyl.
6. method according to claim 3 is it is characterised in that described lewis' acid includes nickel salt, mantoquita, iron salt, pink salt, Or the salt of scandium, yttrium, lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, ytterbium, lutecium.
7. method according to claim 6 is it is characterised in that described salt includes villaumite, sulfate, nitrate, fluoroform Sulfonate or hexafluorophosphate.
8. method according to claim 3 is it is characterised in that also include chloralkane in described reaction medium.
9. method according to claim 3 is it is characterised in that also include dialkylimidazolium salt, institute in described reaction medium The alkyl stating dialkylimidazolium salt is methyl, ethyl, propyl group, butyl, amyl group, hexyl, the anion of described dialkylimidazolium salt For bis trifluoromethyl imines ion, or hexafluorophosphate ion.
10. 1- (5- trifluoromethyl -2- pyridine radicals) sulfydryl-alpha-L- rock algae pyranoside as claimed in claim 2 is in preparation Application in fucosidase diagnostic reagent.
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