Ntxiv nrog rau thev naus laus zis, kev sib txuas ntawm glycosides yeej ib txwm muaj kev txaus siab rau kev tshawb fawb, vim nws yog qhov tshwm sim ntau heev hauv qhov xwm txheej.Cov ntaub ntawv tsis ntev los no los ntawm Schmidt thiab Toshima thiab Tatsuta, nrog rau ntau cov ntaub ntawv hais txog nyob rau hauv, tau tawm tswv yim txog ntau yam khoom muaj peev xwm.
Hauv kev sib xyaw ntawm glycosides, ntau cov suab thaj sib xyaw ua ke nrog cov nucleophiles, xws li cawv, carbohydrates, lossis cov protein, yog tias xaiv cov tshuaj tiv thaiv nrog ib pawg hydroxyl ntawm cov carbohydrates hauv qhov xav tau, tag nrho lwm yam haujlwm yuav tsum tau tiv thaiv hauv thawj kauj ruam.Raws li txoj cai, cov txheej txheem enzymatic lossis microbial, vim lawv cov kev xaiv, tuaj yeem hloov cov tshuaj tiv thaiv thiab kev tiv thaiv cov kauj ruam kom xaiv los ntawm glycosides hauv cheeb tsam.Txawm li cas los xij, vim muaj keeb kwm ntev ntawm alkyl glycosides, daim ntawv thov ntawm enzymes hauv kev sib txuas ntawm glycosides tsis tau kawm dav dav thiab siv.
Vim lub peev xwm ntawm cov enzymes tsim nyog thiab cov nqi tsim khoom siab, enzymatic synthesis ntawm alkyl polyglycosides tsis npaj yuav hloov mus rau qib kev lag luam, thiab cov txheej txheem tshuaj yog nyiam.
Xyoo 1870, MAcolley tau tshaj tawm cov synthesis ntawm "acetochlorhydrose" (1, daim duab 2) los ntawm cov tshuaj tiv thaiv dextrose (glucose) nrog acetyl chloride, uas nws thiaj li coj mus rau keeb kwm ntawm glycoside synthesis txoj kev.

Tetra-0-acetyl-glucopyranosyl halides (acetohaloglucoses) tom qab tau pom tias yog cov neeg nruab nrab muaj txiaj ntsig zoo rau kev sib xyaw ua ke ntawm cov ntshiab alkyl glucosides.Xyoo 1879, Arthur Michael tau ua tiav hauv kev npaj qhov tseeb, crystallizable aryl glycosides los ntawm Colley's intermediates thiab phenolates.(Aro-, Daim duab 2).
Nyob rau hauv 1901, Michael lub synthesis rau ntau yam ntawm carbohydrates thiab hydroxylic aglycons, thaum W.Koenigs thiab E.Knorr qhia lawv cov txheej txheem stereoselective glycosidation (Daim duab 3).Cov tshuaj tiv thaiv muaj kev hloov pauv SN2 ntawm cov pa roj carbon monoxide thiab ua haujlwm stereoselectively nrog inversion ntawm configuration, ua piv txwv li α-glucoside 4 los ntawm β-anomer ntawm aceobromoglucose intermediate 3. Koenigs-Knorr synthesis tshwm sim nyob rau hauv muaj nyiaj los yog mercury promotors.

Nyob rau hauv 1893, Emil Fischer tau npaj ib txoj hauv kev sib txawv rau kev sib txuas ntawm alkyl glucosides.Cov txheej txheem no tam sim no paub zoo tias yog "Fischer glycosidation" thiab suav nrog cov tshuaj tiv thaiv acid-catalyzed ntawm glycoses nrog cawv.Txawm li cas los xij, cov ntaub ntawv keeb kwm yuav tsum txawm li cas los xij suav nrog A.Gautier thawj qhov kev sim hauv xyoo 1874, hloov dextrose nrog anhydrous ethanol nyob rau hauv muaj hydrochloric acid.Vim yog qhov kev ntsuam xyuas tsis tseeb, Gautier ntseeg tias nws tau txais "diglucose".Fischer tom qab ntawd qhia tias Gautier's "diglucose" yog qhov tseeb feem ntau yog ethyl glucoside (Daim duab 4).

Fischer tau txhais cov qauv ntawm ethyl glucoside kom raug, raws li tej zaum yuav pom los ntawm keeb kwm furanosidic formula tau npaj.Qhov tseeb, Fischer glycosidation cov khoom yog complex, feem ntau equilibrium mixs ntawm α/β-anomers thiab pyranoside/furanoside isomers uas kuj muaj xws li randomly txuas glycoside oligomers.
Yog li ntawd, ib tus neeg molecular hom tsis yooj yim rau kev cais tawm ntawm Fischer cov tshuaj tiv thaiv sib xyaw, uas tau ua teeb meem loj yav dhau los.Tom qab qee qhov kev txhim kho ntawm txoj kev sib txuas no, Fischer tom qab tau txais kev sib txuas ntawm Koenigs-Knorr rau nws qhov kev tshawb nrhiav.Siv cov txheej txheem no, E.Fischer thiab B.Helferich yog thawj t qhia txog kev sib txuas ntawm cov saw ntev alkyl glucoside uas nthuav tawm cov khoom surfactant hauv xyoo 1911.
Raws li thaum ntxov xyoo 1893, Fischer tau raug pom zoo cov khoom tseem ceeb ntawm alkyl glycosides, xws li lawv cov kev ruaj ntseg siab ntawm oxidation thiab hydrolysis, tshwj xeeb tshaj yog nyob rau hauv alkaline xov xwm.Ob tus yam ntxwv tseem ceeb rau alkyl polyglycosides hauv kev siv surfactant.
Kev tshawb fawb ntsig txog cov tshuaj tiv thaiv glycosidation tseem tab tom ua thiab ntau txoj hauv kev nthuav dav rau glycosides tau tsim nyob rau yav dhau los tsis ntev los no.Qee cov txheej txheem rau kev sib txuas ntawm glycosides tau sau tseg hauv daim duab 5.
Feem ntau, cov txheej txheem tshuaj glycosidation tuaj yeem muab faib ua cov txheej txheem ua rau cov oligomer equilibria nyuaj hauv acid-catalysed glycosyl pauv.

Cov tshuaj tiv thaiv ntawm cov khoom noj carbohydrate kom tsim nyog (Fischer glycosidic cov tshuaj tiv thaiv thiab hydrogen fluoride (HF) cov tshuaj tiv thaiv nrog cov tsis muaj kev tiv thaiv carbohydrate molecules) thiab kinetics tswj, irreversible, thiab feem ntau stereotaxic hloov cov tshuaj tiv thaiv.Ib hom txheej txheem thib ob tuaj yeem ua rau kev tsim ntawm ib tus neeg hom es tsis yog hauv kev sib xyaw ua ke ntawm cov tshuaj tiv thaiv, tshwj xeeb tshaj yog thaum ua ke nrog kev txuag pab pawg.Carbohydrates tuaj yeem tawm hauv pawg ntawm ectopic carbon, xws li halogen atoms, sulfonyls, lossis trichloroacetimidate pawg, lossis raug qhib los ntawm cov hauv paus ua ntej hloov mus rau triflate esters.
Hauv cov xwm txheej tshwj xeeb ntawm glycosidations hauv hydrogen fluoride lossis hauv kev sib xyaw ntawm hydrogen fluoride thiab pyridine (pyridinium poly [hydrogen fluoride]), glycosyl fluorides yog tsim nyob rau hauv situ thiab smoothly hloov mus rau hauv glycosides, piv txwv li nrog cawv.Hydrogen fluoride tau pom tias yog ib qho kev ua kom muaj zog, tsis muaj kev cuam tshuam qhov nruab nrab;equilibrium nws pib condensation (oligomerization) yog pom zoo ib yam li cov txheej txheem Fischer, txawm hais tias cov tshuaj tiv thaiv mechanism tej zaum txawv.
Cov tshuaj ntshiab alkyl glycosides tsuas yog tsim rau cov ntawv tshwj xeeb heev.Piv txwv li, alkyl glycosides tau siv ua tiav hauv kev tshawb fawb biochemical rau crystallization ntawm daim nyias nyias, xws li peb seem crystallization ntawm porin thiab bacteriorhodopsin nyob rau hauv lub xub ntiag ntawm octyl β-D-glucopyranoside (kev sim ntxiv raws li txoj haujlwm no ua rau Nobel. khoom plig hauv chemistry rau Deisenhofer, Huber thiab Michel hauv 1988).
Thaum lub sij hawm ntawm txoj kev loj hlob ntawm alkyl polyglycosides, stereoselective txoj kev tau siv nyob rau hauv lub chaw soj nstuam ntsuas los ua ke ntau yam qauv tshuaj thiab kawm txog lawv physicochemical zog, vim lawv complexity, instability ntawm intermediates thiab tus nqi thiab tseem ceeb ntawm cov txheej txheem. khib nyiab, syntheses ntawm Koenigs-Knorr hom thiab lwm yam kev tiv thaiv pab pawg neeg yuav tsim teeb meem kev lag luam thiab kev lag luam.Fischer-hom txheej txheem yog qhov sib piv tsis tshua muaj teeb meem thiab yooj yim dua rau kev ua lag luam ntawm kev lag luam thiab raws li, yog txoj kev nyiam rau kev tsim cov alkyl polyglycosides ntawm qhov loj.