-transparent.png){kind=logo}
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.
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
November 1987,
Carbohydrate research,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
October 1967,
Chemical & pharmaceutical bulletin,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
April 1967,
Chemical & pharmaceutical bulletin,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
August 2008,
Bioorganic & medicinal chemistry,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
April 1994,
Carbohydrate research,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
October 1948,
Helvetica chimica acta,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
January 1975,
Journal of the Chemical Society. Perkin transactions 1,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
November 1983,
The International journal of applied radiation and isotopes,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
June 1975,
The Journal of organic chemistry,
A Matsuda, and
K Pankiewicz, and
B K Marcus, and
K A Watanabe, and
J J Fox
March 1947,
Helvetica chimica acta,
