Abstract
The NH,NH-dihydrocycloadduct 1 (6-chloro-9,9-dimethyl-7,8-dihydro-9H-pyrazolo[4,3-d]tetrazolo[1,5-b]-pyridazine) obtained by the cycloaddition of 2-diazopropane to 6-chlorotetrazolo[1,5-b]pyridazine, is transformed with protected or unprotected carbohydrates 2, 5, 7,9, 11, 13 and 15 in the presence of methyl acrylate (3) into the corresponding C-nucleosides 4, 6, 8, 10, 12, 14 and 16. In this one-pot synthesis two new chiral centers are formed stereoselectively, dependent on the chirality at C-atom next to aldehydo group in the carbohydrate
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