Die Umsetzung von Saccharose (I) mit Methansulfonsäurechlorid (II) und nachfolgende Acetylierung mit Acetanhydrid (III) liefert trennbare Gemische mesylierter Saccharose‐acetate (IV).
PBSTRACIOctamolar tosylation of sucrose with p-toluonosulfonyl~tosyl) hlor do has boon ro-oxaninod under diffrront conditions to obtain octa-0-tosyl sucrose as a singlo ontity.It was obsorvod that tosylation of sucrose with 8 molos of tosyl chlorido in pyridino at O a C , -5.C and -15.C affordod octa -0-tosyl sucrosr. hopta-0-tosyl sucrosr. hrxa-0-tory1 sucrose and ponta-0tosyl sucroso rrspoctivoly in varying amounts. Tho products obtainrd uoro purifiod by column chromatography and tho structuros of th chromatographically puro tosyl ostors uorr confirmrd by high rrrolution 'H NMR spoctra of thoir rospoctivo acotatos.
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Proparation of rcyl dorivrtivos of carbohydratos is vory well oxploitod in tho fioldof monosaccharidrs (I).Tho thrust has rocontly born shiftod to proparo tho acyl dorivativos of oligosaccharidrs (2-12) to study tho chomistry of oligosaccharidos in drtail so that tho fiold can bo oxploitod for its' commorcial potontial in tho futuro.
Hockrtt and Zirf (2) roportod tho formation of sulfonyl ostors of sucroso as oarly as in 1950 to obtain octa-0-mosyl. octa-O-tosylr andtri-0-tosyl sucrosrs. In our attempt to proparr octa-0-tosyl s u~r o s o~ with tho objrctivr to us. it as a prrcursor for making polyfunctional dorivatives of sucrosr, it was obsorvod that in no caso octa-0-tosyl sucroso uas obtainod as tho singlo and major ontity. Honco, tho intorost uas croatod to ro-oxamino tho octamolar tosylation of sucroso undor diffrront conditions.In tho prosont work attompts uoro mad. to proparo octa-0-tosyl sucrose at difforont tomprraturos varying from -1S.C to 80.C by tho mothod of Hockott and Zirf (2). In a11 tho casos i t was notod that tho products obtainrd urro mixturrs of diffrront tosyl sucrosos in various yirlds with +Prosont addross: Stat.
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