A new synthesis ofL-talose and preparation of its adenine nucleosides

✍ Scribed by Leon M. Lerner; Gary Mennitt

• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 783 KB
• Volume: 259
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)84057-1

✦ Synopsis

Methyl 2,3-0-isopropylidene-S,6-di-D-methylsulfonyl-l3-n-allofuranoside, prepared by a route starting from n-glucose and its conversion to 1,2: S,6-di-O-isopropylidene-a-D-allofuranose and n-allose, has been used as the starting material for a new synthesis of L-talose. The configuration at e-S was inverted with NaOAc in hot DMF, resulting in the i-talofuranoside derivative from which the acetyl groups were removed to give methyl 2,3-0-isopropylidene-a-L-talofuranoside. Hydrolysis of the latter yielded t-talose, Methyl 2,3-0-isopropylidene-a-L-talofuranoside was used as the starting material in a six-step synthesis of 9-a-L-talofuranosyladenine. L-Talose was acetylated and coupled with the base to give 9-a-L-talopyranosyladenine. 9-a-L-Talofuranosyladenine was a slow-reacting substrate for calf intestinal adenosine deaminase (adenosine aminohydrolase, EC 3.5.4.4) and an inhibitor of the growth of leukemia L1210 cells in vitro.