A new protecting group for the 5'-hydroxyl group having O-S single bond oxidatively cleavable under mild conditions.
We developed a new protecting group, ie., cis-[4-[[(4-methoxytrityl)sulfenyl]oxy]tetrahydrofuran-3-yl]oxycarbonyl (MTFOC), which could be removed under neutral conditions involving the oxidative removal of the MMTrS group followed by the self-cyclization of the resulting intermediate. The introduction of the protecting group into the 5-hydroxyl group of a thymidine derivative and its deprotection were studied.
Utagawa
Eri
E
Department of Life Science, Tokyo Institute of Technology, Yokohama, Japan.
Seio
Kohji
K
Sekine
Mitsuo
M
D002384:Catalysis; D005663:Furans / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry; D017665:Hydroxyl Radical; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods*; D009841:Oligonucleotides / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry; D013936:Thymidine / Q000737:chemistry
D005663:Furans; D006878:Hydroxides; D009841:Oligonucleotides; D017665:Hydroxyl Radical; C018674:tetrahydrofuran; D013455:Sulfur; C031356:hydroxide ion; D010100:Oxygen; D013936:Thymidine