Carbohydrate research p. 297 - 302 (1982)
Update date:2022-07-30
Topics:
Matsuda
Pankiewicz
Marcus
Watanabe
Fox
The first chemical synthesis of 3-methyl-psi-uridine (5) and its 2'-deoxy analogue (9) has been achieved. psi-Uridine was trimethylsilylated and the crude product was treated with acetyl chloride, to give the 1-acetyl derivative (3). Crude 3 was methylated with dimethoxymethyldimethylamine and then saponified, to give crystalline 5 in 82% overall yield. Treatment of 5 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane afforded the 3'5'-protected product, which was converted into the 2'O-[(imidazol-1-yl) thiocarbonyl] derivative 7. Reduction of 7 with tributyltin hydride followed by deblocking of the product gave crystalline 2'-deoxy-3-methyl-psi-uridine (9) in 35% yield form 5.
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Doi:10.1021/jacs.6b04781
(2016)Doi:10.1016/S0040-4039(00)86824-0
(1982)Doi:10.1016/0022-1139(95)03332-7
(1996)Doi:10.1016/j.ica.2004.06.022
(2004)Doi:10.1021/jo00137a029
(1982)Doi:10.1055/s-2004-832838
(2004)
