Ngaphezu kobuchwepheshe, ukuhlanganiswa kwe-glycosides bekulokhu kuthakazelisa isayensi, njengoba kuwukusabela okuvamile emvelweni.Amaphepha akamuva kaSchmidt noToshima kanye noTatsuta, kanye nezikhombo eziningi ezicashunwe lapho, ziye zaphawula ngezinhlobonhlobo zamandla okwenziwa.
Ekuhlanganisweni kwe-glycosides, izakhi ezinoshukela omningi zihlanganiswa nama-nucleophile, afana notshwala, ama-carbohydrate, noma amaprotheni, uma ukusabela okukhethiwe kwelinye lamaqembu e-hydroxyl e-carbohydrate edingekayo, yonke eminye imisebenzi kufanele ivikelwe isinyathelo sokuqala.Eqinisweni, izinqubo ze-enzymatic noma ze-microbial, ngenxa yokukhetha kwazo, zingangena esikhundleni sezinyathelo zokuvikela amakhemikhali eziyinkimbinkimbi kanye nezinyathelo zokuvikela ngokukhetha kusuka kuma-glycosides ezifundeni.Kodwa-ke, ngenxa yomlando omude we-alkyl glycosides, ukusetshenziswa kwama-enzyme ekuhlanganiseni kwe-glycosides akuzange kufundwe kabanzi futhi kusetshenziswe.
Ngenxa yomthamo wezinhlelo zama-enzyme afanelekile kanye nezindleko zokukhiqiza eziphezulu, ukuhlanganiswa kwe-enzymatic kwe-alkyl polyglycosides akukakalungeli ukuthuthukiswa ezingeni lezimboni, futhi kukhethwa izindlela zamakhemikhali.
Ngo-1870, i-MAcolley yabika ukuhlanganiswa kwe-“acetochlorhydrose”(1,figure2) ngokusabela kwe-dextrose(glucose) nge-acetyl chloride, okwagcina kuholele kumlando wemizila ye-glycoside synthesis.

I-Tetra-0-acetyl-glucopyranosyl halides(acetohaloglucoses) kamuva kwatholakala ukuthi iwusizo ekuhlanganiseni kwe-stereoelective synthesis ye-alkyl glucosides emsulwa.Ngo-1879, u-Arthur Michael waphumelela ekulungiseleleni ama-aryl glycosides aqondile, ahlanzekile avela ku-Colley's intermediate kanye nama-phenolate.(I-Aro-, Umfanekiso 2).
Ngo-1901, ukuhlanganiswa kukaMichael kuhlu olubanzi lwamacarbohydrates nama-hydroxylic aglycons, lapho u-W.Koenigs no-E.Knorr bethula inqubo yabo ethuthukisiwe ye-stereoelective glycosidation(Umfanekiso 3).Ukusabela kuhilela ukufaka esikhundleni se-SN2 ku-anomeric carbon futhi kuqhubeka ngokuzenzakalelayo ngokuguqulwa kokumisa, ukukhiqiza isibonelo i-α-glucoside 4 kusukela ku-β-anomer ye-aceobromoglucose emaphakathi 3. Ukuhlanganiswa kwe-Koenigs-Knorr kwenzeka phambi kwesiliva noma abathuthukisi be-mercury.

Ngo-1893, u-Emil Fischer wahlongoza indlela ehluke kakhulu ekuhlanganiseni ama-alkyl glucosides.Le nqubo manje yaziwa kakhulu ngokuthi "i-Fischer glycosidation" futhi ihlanganisa ukusabela kwe-acid-catalyzed kwama-glycoses notshwala.Noma iyiphi i-akhawunti yomlando kufanele nokho ihlanganise nomzamo wokuqala obikiwe we-A. Gautier ngo-1874, wokuguqula i-dextrose nge-anhydrous ethanol phambi kwe-hydrochloric acid.Ngenxa yokuhlaziya okuyisisekelo okudukisayo, uGautier ukholelwa ukuthi uthole “i-diglucose”.UFischer kamuva wabonisa ukuthi “i-diglucose” kaGautier empeleni yayiyi-ethyl glucoside (Umfanekiso 4).

UFischer wachaza ukwakheka kwe-ethyl glucoside ngendlela efanele, njengoba kungase kubonakale kufomula yomlando ye-furanosidic ehlongozwayo.Eqinisweni, imikhiqizo ye-Fischer glycosidation iyinkimbinkimbi, ikakhulukazi izingxube ezilinganayo ze-α/β-anomers kanye ne-pyranoside/furanoside isomers nayo ehlanganisa ama-oligomers e-glycoside axhunywe ngokungahleliwe.
Ngakho-ke, uhlobo olulodwa lwamangqamuzana akulula ukuluhlukanisa nezingxube zokusabela kwe-Fischer, obekuyinkinga enkulu esikhathini esidlule.Ngemva kokuthuthukiswa okuthile kwale ndlela yokuhlanganisa, uFischer wabe esethatha i-Koenigs-Knorr synthesis ocwaningweni lwakhe.Ngokusebenzisa le nqubo, u-E.Fischer kanye no-B.Helferich babengabokuqala t babika ukuhlanganiswa kwe-alkyl glucoside yochungechunge olude ebonisa izakhiwo ze-surfactant ngo-1911.
Kusukela ngo-1893, uFischer wayezibone kahle izici ezibalulekile ze-alkyl glycosides, njengokuzinza kwazo okuphezulu ku-oxidation kanye ne-hydrolysis, ikakhulukazi emithonjeni ye-alkaline enamandla.Zombili izici zibalulekile kuma-alkyl polyglycosides ekusetshenzisweni kwe-surfactant.
Ucwaningo oluhlobene nokusabela kwe-glycosidation lusaqhubeka futhi imizila eminingana ethokozisayo eya kuma-glycoside yenziwe esikhathini esidlule.Ezinye zezinqubo zokwenziwa kwama-glycosides zifingqiwe kuMfanekiso 5.
Ngokuvamile, izinqubo ze-glycosidation zamakhemikhali zingahlukaniswa zibe izinqubo eziholela ekulinganeni kwe-oligomer eyinkimbinkimbi ekushintshisaneni kwe-acid-catalysed glycosyl.

Ukusabela kuma-carbohydrate acushwe ngokufanelekile(ukusabela kwe-Fischer glycosidic kanye nokusabela kwe-hydrogen fluoride(HF) nama-molecule e-carbohydrate angavikelekile) kanye ne-kinetics elawulwayo, engenakuhlehliswa, futhi ikakhulukazi ukusabela kwe-stereotaxic.Uhlobo lwesibili lwenqubo lungase luholele ekwakhekeni kwezinhlobo zohlobo ngalunye kunokuba kube yingxube eyinkimbinkimbi yokusabela, ikakhulukazi uma kuhlanganiswe namasu eqembu lokulondoloza.Ama-carbohydrate angase ashiye amaqembu ku-ectopic carbon, njengama-athomu e-halogen, ama-sulfonyls, noma amaqembu e-trichloroacetimidate, noma enziwe asebenze ngezisekelo ngaphambi kokuguqulelwa ku-triflate esters.
Esimeni esithile se-glycosidations ku-hydrogen fluoride noma kuzingxube ze-hydrogen fluoride ne-pyridine (pyridinium poly [hydrogen fluoride]), i-glycosyl fluoride yakheka ku-situ futhi iguqulwa kahle ibe ama-glycosides, isibonelo ngotshwala.I-Hydrogen fluoride iboniswe iyindlela yokusabela enamandla, engasebenzi kahle;i-equilibrium auto condensation(oligomerization) ibonakala ifana nenqubo ye-Fischer, nakuba indlela yokusabela cishe ihlukile.
Ama-alkyl glycosides ahlanzekile ngamakhemikhali afaneleka kuphela ukusetshenziswa okukhethekile kakhulu.Isibonelo, i-alkyl glycosides isetshenziswe ngempumelelo ocwaningweni lwamakhemikhali ezinto eziphilayo ukuze kucwebezeliswe amaprotheni olwelwesi lwama-membrane, njenge-crystallization ye-porin enezinhlangothi ezintathu ne-bacteriorhodopsin phambi kwe-octyl β-D-glucopyranoside (olunye ucwaningo olusekelwe kulo msebenzi luholela kuNobel. umklomelo kukhemistri kaDeisenhofer, uHuber noMichel ngo-1988).
Ngesikhathi sokuthuthukiswa kwe-alkyl polyglycosides, kusetshenziswe izindlela ze-stereoselective esikalini selabhorethri ukuze kuhlanganiswe izinhlobonhlobo zezinto eziyimodeli nokufunda izakhiwo zazo ze-physicochemical, ngenxa yobunzima bazo, ukungazinzi kweziphakathi kanye nenani kanye nesimo esibucayi senqubo. ama-wasters, ama-syntheses ohlobo lwe-Koenigs-Knorr namanye amasu eqembu lokuvikela angadala izinkinga ezinkulu zobuchwepheshe nezomnotho.Izinqubo zohlobo lwe-Fischer aziyinkimbinkimbi ngokuqhathaniswa futhi zilula ukuzenza esikalini sezentengiselwano futhi ngokufanelekile, ziyindlela ekhethwayo yokukhiqiza ama-alkyl polyglycosides ngezinga elikhulu.