Synthesis of 2',3'-dideoxyinosine via radical deoxygenation.
A synthetic method for 2',3'-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5'-O-diprotected-2',3'-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at the N1, 5'-O-positions were effective for the ddI synthesis.
Torii
Takayoshi
T
AminoScience Laboratories, Ajinomoto Co., Inc., Kawasaki, Japan.
Izawa
Kunisuke
K
Cho
Dae Hyan
DH
Jang
Doo Ok
DO
D016049:Didanosine / Q000138:chemical synthesis* / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D008722:Methods; D010084:Oxidation-Reduction; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry
D005609:Free Radicals; D018894:Reverse Transcriptase Inhibitors; D016049:Didanosine