Synthesis and reactivities of 2,2'-anhydro-1-(3'-deoxy-3'-iodo-5'-O-trityl- beta-D-arabinofuranosyl)thymine.
2,2'-Anhydro-1-(3'-deoxy-3'-iodo-5'-O-trityl-beta-D-arabinofuranosyl) thymine (2) was synthesized from 2',3'-didehydro-3'-deoxythymidine (DHT). Compound 2 was readily converted into the 2',3'-anhydrolyxofuranosyl derivatives 4-6. Treatment of 4a with some nucleophiles (N3-, OMe-, Cl-) gave the corresponding 3'-substituted arabinosyl nucleosides (7a,c,e) together with the minor xylosyl isomers (8a,c,d). 7a,c,e were deprotected to 7b,d,f, respectively.
Minamoto
K
K
Department of Applied Chemistry, School of Engineering, Nagoya University, Japan.
Hamano
Y
Y
Matsuoka
Y
Y
Watanabe
K
K
Eguchi
S
S
D015224:Dideoxynucleosides / Q000737:chemistry; D015394:Molecular Structure; D018119:Stavudine; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D015224:Dideoxynucleosides; C077693:2,2'-anhydro-1-(3'-deoxy-3'-iodoarabinofuranosyl)thymine; D018119:Stavudine; D013936:Thymidine