Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues.
The reaction of thymidine, 3-mono-, and 3,3',5'-trialkylsubstitued thymidine analogues with iodine monochloride (ICl) was investigated. Treatment with ICl resulted in rapid deglycosylation, anomerization, and isomerization of thymidine and 3-substituted thymidine analogues under various reaction conditions leading to the formation of the nucleobases as the major products accompanied by minor formation of α-furanosidic-, α-pyranosidic-, and β-pyranosidic nucleosides. On the other hand, 3,3',5'-trisubstitued thymidine analogues were only deglycosylated and anomerized. These results are similar to those observed for the acidic hydrolysis of the glycoside bond in nucleosides, but were presumably caused by the Lewis acid character of an iodine electrophile.
a Division of Medicinal Chemistry & Pharmacognosy, College of Pharmacy , The Ohio State University , Columbus , Ohio.
Ahmed
A
Khalil
Keisuke
K
Ishita
Tehane
T
Ali
Rohit
R
Tiwari
Ramy
R
Riachy
Antonio
A
Toppino
Sherifa
S
Hasabelnaby
Naum
N
Sayfullin
Allen G
AG
Oliver
Judith
J
Gallucci
Zhenguo
Z
Huang
Werner
W
Tjarks
D002712:Chlorides / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D006868:Hydrolysis; D007454:Iodides / Q000737:chemistry*; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry*
D002712:Chlorides; D006027:Glycosides; D007454:Iodides; C009813:iodine monochloride; D013936:Thymidine
3-Substituted thymidine analogues; anomerization; deglycosylation; iodine monochloride; isomerization