Glycosidation of 2, 3, 6-trideoxy-3-trifluoroacclamido-4-
O-tritluoroacetyl-α-D-
arabino-hexopyranosyl chloride (
19) (or the corresponding 4-
p-nitrobenzoate,
20) with daunomycinone under KOENIGS-KNORR conditions afforded, after separation of the anomers and removal of the protecting groups, the individual target glycosides
8 (α anomer; major product) and
9 (β; minor) in acceptable yields. In contrast, the title diamino sugar, suitably protected with
N-trifluoroacetyl and
O-acetyl (or
O-
p-nitrobenzoyl) groups, underwent stereospecific coupling to the anthracycline aglycon by the glycal procedure to give, after deprotection, the α glycoside
12. All three analogs were assayed
in vivo against P388 lymphocytic leukemia. They showed little (T/C 125 for
8; T/C 115 for
9) or no (compound
12) activity, but were essentially devoid of toxicity at the dose-levels tested.
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