Marka lagu daro tignoolajiyada, isku-dhafka glycosides ayaa had iyo jeer xiiseynaya sayniska, maadaama ay tahay falcelin aad u badan oo dabiiciga ah.Waraaqihii ugu dambeeyay ee Schmidt iyo Toshima iyo Tatsuta, iyo sidoo kale tixraacyo badan oo lagu soo qaatay, ayaa ka faallooday awoodo fara badan oo isku dhafan.
Marka la isku daro glycosides, qaybo badan oo sonkor ah ayaa lagu daraa nucleophiles, sida aalkolada, karbohaydraytyada, ama borotiinka, haddii falcelinta xulashada mid ka mid ah kooxaha hydroxyl ee karbohaydrayt loo baahan yahay, dhammaan hawlaha kale waa in lagu ilaaliyo talaabada ugu horeysa.Mabda 'ahaan, hababka enzymatic ama microbial, sababtoo ah doorashadooda, waxay bedeli karaan ilaalinta kiimikada adag iyo tillaabooyinka ilaalinta si ay si xushmad leh uga soo baxaan glycosides ee gobollada.Si kastaba ha ahaatee, sababtoo ah taariikhda dheer ee alkyl glycosides, codsiga enzymes ee isku dhafka glycosides si weyn looma baran oo looma adeegsan.
Sababtoo ah awoodda nidaamyada enzyme ee ku habboon iyo kharashyada wax soo saarka sare, isku-dhafka enzymatic ee alkyl polyglycosides diyaar uma aha in la cusboonaysiiyo heerka warshadaha, hababka kiimikada ayaa la door bidaa.
1870-kii, MAcolley wuxuu soo sheegay isku-dhafka "acetochlorhydrose"(1,figure2) ee falcelinta dextrose (glucose) oo leh chloride acetyl, taas oo ugu dambeyntii keentay taariikhda waddooyinka isku-dhafka glycoside.

Tetra-0-acetyl-glucopyranosyl halides (acetohaloglucoses) ayaa markii dambe la ogaaday inay dhexdhexaadiyayaal faa'iido leh u yihiin isku-dhafka stereoselective ee alkyl glucosides saafi ah.Sannadkii 1879-kii, Arthur Michael waxa uu ku guulaystay in uu diyaariyo aryl glycosides qeexan oo ka yimi dhexdhexaadiyeyaasha Colley iyo phenolates.(Aro-, Sawirka 2).
Sannadkii 1901, isku-dubaridkii Michael ee karbohaydraytyo kala duwan iyo aglycons hydroxylic, markii W.Koenigs iyo E.Knorr ay soo bandhigeen hannaankooda glycosidation stereoselective (Jaantuska 3).Dareen-celinta waxay ku lug leedahay beddelka SN2 ee kaarboonka anomeric waxayna u socotaa si isdaba-joog ah iyadoo la rogayo qaabeynta, soo saarista tusaale ahaan α-glucoside 4 oo ka soo jeeda β-anomer ee dhexdhexaadiyaha aceobromoglucose 3. Isku-darka Koenigs-Knorr wuxuu ku dhacaa joogitaanka lacag ama lacag. dhiirrigeliyeyaasha meerkuriga.

Sannadkii 1893-kii, Emil Fischer waxa uu soo jeediyay hab aasaasi ah oo ka duwan hab-samaynta alkyl glucosides.Nidaamkan hadda waxaa si fiican loogu yaqaan "Fischer glycosidation" wuxuuna ka kooban yahay falcelinta acid-catalyzed ee glycoses leh alkolada.Xisaab kasta oo taariikhi ah si kastaba ha ahaatee waa in lagu daro isku daygii ugu horreeyay ee A.Gautier ee la soo sheegay 1874, si loogu beddelo dextrose leh ethanol anhydrous iyadoo joogitaanka hydrochloric acid.Falanqaynta asaasiga ah ee marin habaabinta awgeed, Gautier wuxuu rumaysnaa inuu helay "diglucose".Fischer ayaa markii dambe muujiyay in Gautier's "diglucose" uu dhab ahaantii ahaa ethyl glucoside (Jaantus 4).

Fischer wuxuu si sax ah u qeexay qaabka ethyl glucoside, sida laga yaabo in laga arko qaacidada furanosidic ee taariikhiga ah ee la soo jeediyay.Dhab ahaantii, alaabta Fischer glycosidation waa mid adag, inta badan isku-darka dheellitirka ee α / β-anomers iyo pyranoside / furanoside isomers kuwaas oo sidoo kale ka kooban oligomers glycoside si aan kala sooc lahayn.
Sidaas awgeed, noocyada unugyadu ma fududa in laga go'doomiyo isku-darka falcelinta Fischer, taas oo ahayd dhibaato halis ah waagii hore.Ka dib waxoogaa horumar ah oo lagu sameeyay habkan isku-dhafka ah, Fischer wuxuu markaa ka dib qaatay isku-darka Koenigs-Knorr ee baaritaankiisa.Isticmaalka habkan, E.Fischer iyo B.Helferich waxay ahaayeen kuwii ugu horreeyay ee t ka warbixiya isku dhafka silsiladda dheer ee alkyl glucoside oo soo bandhigaysa alaabada surfactant 1911kii.
Horaantii 1893, Fischer wuxuu si sax ah u ogaaday sifooyinka muhiimka ah ee alkyl glycosides, sida xasiloonidooda sare ee oksaydhka iyo hydrolysis, gaar ahaan warbaahinta xooggan ee alkaline.Labada sifo waxay qiimo u leeyihiin alkyl polyglycosides ee codsiyada surfactant.
Cilmi-baaris la xiriirta fal-celinta glycosidation ayaa wali socota waxaana dhowr waddo oo xiiso leh loo sameeyay glycosides ayaa la sameeyay dhawaanahan.Qaar ka mid ah hababka isku dhafka glycosides ayaa lagu soo koobay sawirka 5.
Guud ahaan, hababka glycosidation kiimikaad waxaa loo qaybin karaa habab horseeda isku dheelitirnaanta oligomer adag ee beddelka glycosyl-ka-catalysed glycosyl.

Falcelinta ku saabsan substrate-ka karbohaydrayt ee ku habboon ee firfircoon (Fischer glycosidic reactions iyo hydrogen fluoride (HF) falcelinta leh unugyada karbohaydrayt ee aan la ilaalin) iyo kinetics la xakameeyey, aan laga noqon karin, iyo badiyaa falcelinta beddelka stereotaxic.Nooca labaad ee habraaca ayaa laga yaabaa inuu u horseedo samaynta noocyada shakhsi ahaaneed halkii ay ka ahaan lahaayeen isku-dhafka isku dhafan ee falcelinta, gaar ahaan marka lagu daro farsamooyinka kooxda ilaalinta.Carbohydratesku waxay kaga tagi karaan kooxaha kaarboonka ectopic-ka ah, sida atamka halogen, sulfonyls, ama kooxaha trichloroacetimidate, ama waxaa lagu dhaqaajiyaa saldhigyada ka hor inta aan loo beddelin esters triflate.
Xaaladda gaarka ah ee glycosidations ee fluoride hydrogen ama isku dhafka hydrogen fluoride iyo pyridine (pyridinium poly [hydrogen fluoride]), glycosyl fluoride ayaa lagu sameeyay goobta waxaana si habsami leh loogu beddelaa glycosides, tusaale ahaan khamriga.Hydrogen fluoride waxa la tusay in uu yahay falcelin xoog leh oo firfircoon oo aan hoos u dhicin;Isku dheelitirnaanta auto-condensation (oligomerization) ayaa loo arkaa mid la mid ah habka Fischer, in kasta oo habka falcelinta ay u badan tahay inuu ka duwan yahay.
Kiimikada saafiga ah alkyl glycosides waxay kaliya ku habboon yihiin codsiyada gaarka ah.Tusaale ahaan, alkyl glycosides ayaa si guul leh loogu isticmaalay cilmi-baarista biochemical ee kicinta borotiinka xuubabka, sida saddex-geeska ah crystallization of porin iyo bacteriorhodopsin iyadoo ay joogaan octyl β-D-glucopyranoside abaal-marin xagga kimistariga ah ee Deisenhofer, Huber iyo Michel sanadkii 1988).
Inta lagu guda jiro koorsada horumarinta alkyl polyglycosides, hababka stereoselective ayaa loo isticmaalay qiyaasta shaybaarka si ay u soo saaraan noocyo kala duwan oo maaddooyinka model ah iyo in la barto sifooyinkooda physicochemical, sababtoo ah kakanaanta, xasiloonida dhexdhexaadiyeyaasha iyo qadarka iyo dabeecadda muhiimka ah ee habka. qashinka, isku-dhafka nooca Koenigs-Knorr iyo farsamooyinka kale ee kooxda ilaalinta ayaa abuuri doona dhibaatooyin farsamo iyo dhaqaale oo muhiim ah.Nidaamyada nooca Fischer marka la barbar dhigo way ka dhib yar yihiin wayna fududahay in lagu fuliyo miisaan ganacsi, sidaas awgeed, waa habka la door bidayo ee soo saarista alkyl polyglycosides si baaxad leh.