Kuphatikiza paukadaulo, kaphatikizidwe ka glycosides nthawi zonse kwakhala kosangalatsa kwa sayansi, chifukwa ndizofala kwambiri m'chilengedwe. Mapepala aposachedwapa a Schmidt ndi Toshima ndi Tatsuta, komanso maumboni ambiri otchulidwa mmenemo, anenapo za kuthekera kosiyanasiyana kopanga.
Mu kaphatikizidwe ka glycosides, magawo a shuga ambiri amaphatikizidwa ndi ma nucleophiles, monga ma alcohols, chakudya, kapena mapuloteni, ngati chosankha chimodzi mwamagulu a hydroxyl cha carbohydrate chikufunika, ntchito zina zonse ziyenera kutetezedwa. sitepe yoyamba. M'malo mwake, njira za enzymatic kapena tizilombo tating'onoting'ono, chifukwa cha kusankha kwawo, zimatha kulowa m'malo ovuta kuteteza mankhwala ndi njira zodzitetezera kuti zisankhe kuchokera ku glycosides m'zigawo. Komabe, chifukwa cha mbiri yakale ya alkyl glycosides, kugwiritsa ntchito ma enzymes mu kaphatikizidwe ka glycosides sikunaphunzire kwambiri ndikugwiritsidwa ntchito.
Chifukwa cha mphamvu zama enzyme oyenerera komanso mtengo wokwera wopangira, kaphatikizidwe ka enzymatic ka alkyl polyglycosides sikuli wokonzeka kukwezedwa mpaka pamlingo wa mafakitale, ndipo njira zama mankhwala zimakondedwa.
Mu 1870, MAcolley adanenanso za kaphatikizidwe ka "acetochlorhydrose" (1, chithunzi2) potengera dextrose (glucose) ndi acetyl chloride, zomwe zidatsogolera ku mbiri ya njira zopangira glycoside.

Tetra-0-acetyl-glucopyranosyl halides(acetohaloglucoses) pambuyo pake zinapezeka kuti ndizothandiza pakupanga stereoselective synthesis ya alkyl glucosides oyera. Mu 1879, Arthur Michael adakwanitsa kukonza ma aryl glycosides otsimikizika, opangidwa kuchokera ku Colley's intermediates ndi phenolates. (Aro-, Chithunzi 2).
Mu 1901, kaphatikizidwe ka Michael kumitundu yambiri yama carbohydrate ndi ma hydroxylic aglycons, pomwe W.Koenigs ndi E.Knorr adayambitsa njira yawo yosinthira stereoselective glycosidation (Chithunzi 3). Zomwe zimapangidwira zimaphatikizapo kulowetsedwa kwa SN2 pa anomeric carbon ndikupita patsogolo mosasintha ndi kusinthika kwa kasinthidwe, kupanga mwachitsanzo α-glucoside 4 kuchokera ku β-anomer ya aceobromoglucose yapakati 3. Koenigs-Knorr synthesis imachitika pamaso pa siliva kapena siliva kapena siliva. othandizira mercury.

Mu 1893, Emil Fischer anapereka njira yosiyana kwambiri ndi kaphatikizidwe ka alkyl glucosides. Njira imeneyi tsopano imadziwika bwino kuti "Fischer glycosidation" ndipo imakhala ndi acid-catalyzed reaction of glycoses with alcohols. Nkhani iliyonse yakale iyeneranso kuphatikiza kuyesa koyamba kwa A. Gautier mu 1874, kusintha dextrose ndi anhydrous ethanol pamaso pa hydrochloric acid. Chifukwa cha kusanthula kolakwika, Gautier adakhulupirira kuti adapeza "diglucose". Pambuyo pake Fischer adawonetsa kuti "diglucose" ya Gautier kwenikweni inali ethyl glucoside (Chithunzi 4).

Fischer adalongosola bwino momwe ethyl glucoside imapangidwira, monga momwe tingawonere kuchokera ku mbiri yakale ya furanosidic formula yoperekedwa. Ndipotu, mankhwala a Fischer glycosidation ndi ovuta, makamaka osakaniza osakanikirana a α/β-anomers ndi pyranoside/furanoside isomers omwe amakhalanso ndi oligomers ogwirizana mwachisawawa.
Chifukwa chake, mitundu ya mamolekyu pawokha sikophweka kudzipatula ku Fischer reaction mix, yomwe idakhala vuto lalikulu m'mbuyomu. Pambuyo pakusintha pang'ono kwa njira yophatikizira iyi, Fischer adatengera kaphatikizidwe ka Koenigs-Knorr pakufufuza kwake. Pogwiritsa ntchito njirayi, E.Fischer ndi B.Helferich anali oyamba t kulengeza za kaphatikizidwe ka unyolo wautali wa alkyl glucoside wowonetsa zinthu zopezeka mu 1911.
Kumayambiriro kwa 1893, Fischer adawona molondola zofunikira za alkali glycosides, monga kukhazikika kwawo kwa okosijeni ndi hydrolysis, makamaka muzofalitsa zamphamvu zamchere. Makhalidwe onsewa ndi ofunika kwa ma alkyl polyglycosides pakugwiritsa ntchito surfactant.
Kafukufuku wokhudzana ndi momwe glycosidation amachitira akadali akupitilira ndipo njira zingapo zosangalatsa zopita ku glycosides zapangidwa posachedwa. Zina mwa njira zopangira ma glycosides zafotokozedwa mwachidule Chithunzi 5.
Mwambiri, njira za glycosidation zamankhwala zitha kugawidwa m'njira zomwe zimatsogolera ku zovuta za oligomer equilibria mu kusinthana kwa acid-catalysed glycosyl.

Zochita pazagawo zoyendetsedwa bwino zama carbohydrate (Fischer glycosidic reactions and hydrogen fluoride(HF) reaction with unprotected carbohydrate molecules) ndi ma kinetics olamuliridwa, osasinthika, komanso makamaka stereotaxic m'malo. Mtundu wachiwiri wa ndondomeko ukhoza kutsogolera ku mapangidwe amtundu wina m'malo mosakanikirana ndi zochitika, makamaka pamene ziphatikizidwa ndi njira zotetezera gulu. Zakudya zopatsa mphamvu zimatha kusiya magulu pa ectopic carbon, monga ma atomu a halogen, sulfonyls, kapena magulu a trichloroacetimidate, kapena kuyendetsedwa ndi maziko asanatembenuzidwe kukhala triflate esters.
Pankhani ya glycosides mu haidrojeni fluoride kapena zosakaniza za haidrojeni fluoride ndi pyridine (pyridinium poly [hydrogen fluoride]), glycosyl fluorides amapangidwa mu situ ndipo amasinthidwa bwino kukhala glycosides, mwachitsanzo ndi ma alcohols. Hydrogen fluoride adawonetsedwa kuti ndi njira yolimbikitsira kwambiri, yosasinthika; equilibrium auto condensation (oligomerization) imawoneka yofanana ndi njira ya Fischer, ngakhale njira yochitira mwina ndi yosiyana.
Ma alkyl glycosides achilengedwe ndi oyenera kugwiritsa ntchito mwapadera kwambiri. Mwachitsanzo, alkyl glycosides akhala akugwiritsidwa ntchito bwino mu kafukufuku biochemical kwa crystallization wa nembanemba mapuloteni, monga atatu dimensional crystallization wa porin ndi bacteriorhodopsin pamaso pa octyl β-D-glucopyranoside (zowonjezera zina zochokera ntchito imeneyi kutsogolera ku Nobel). mphotho mu chemistry ya Deisenhofer, Huber ndi Michel mu 1988).
Panthawi ya chitukuko cha alkyl polyglycosides, njira zopangira stereoselective zakhala zikugwiritsidwa ntchito pamlingo wa labotale kuti apange zinthu zosiyanasiyana zachitsanzo ndikuwerenga mawonekedwe awo a physicochemical, chifukwa cha zovuta zawo, kusakhazikika kwapakati komanso kuchuluka kwake komanso momwe zimakhalira zovuta. owononga, zophatikizika za mtundu wa Koenigs-Knorr ndi njira zina zodzitetezera zamagulu zitha kubweretsa zovuta zaukadaulo ndi zachuma. Njira zamtundu wa Fischer ndizovuta kwambiri komanso zosavuta kuchita pazamalonda ndipo motero, ndiyo njira yabwino yopangira ma alkyl polyglycosides pamlingo waukulu.