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

Article abstract of DOI:10.1016/0008-6215(94)84057-1

Methyl 2,3-O-isopropylidene-5,6-di-O-methylsulfonyl-β-D-allofuranoside, prepared by a route starting from D-glucose and its conversion to 1,2:5,6- di-O-isopropylidene-α-D-allofuranose and D-allose, has been used as the starting material for a new synthesis of L-talose. The configuration at C-5 was inverted with NaOAc in hot DMF, resulting in the L-talofuranoside derivative from which the acetyl groups were removed to give methyl 2,3-O- isopropylidene-α-L-talofuranoside. Hydrolysis of the latter yielded L- talose. Methyl 2,3-O-isopropylidene-α-L-talofuranoside was used as the starting material in a six-step synthesis of 9-α-L-talofuranosyladenine. L- Talose was acetylated and coupled with the base to give 9-α-L- talopyranosyladenine. 9-α-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. Methyl 2,3-O-isopropylidene-5, 6-di-O-methylsulfonyl-β-D-allofuranoside, prepared by a route starting from D-glucose and its conversion to 1,2:5, 6-di-O-isopropylidene-α-D-allofuranose and D-allose, has been used as the starting material for a new synthesis of L-talose. The configuration at C-5 was inverted with NaOac in hot DMF, resulting in the L-talofuranoside derivative from which the acetyl groups were removed to give methyl 2,3-O-isopropylidene-α-L-talofuranoside. Hydrolysis of the latter yielded L-talose. Methyl 2, 3-O-isopropylidene-α-L-talofuranoside was used as the starting material in a six-step synthesis of 9-α-L-talofuranosyladenine. L-Talose was acetylated and coupled with the base to give 9-α-L-talopyranosyladenine. 9-α-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.