Decilonitrose and 4-O-succinyl-L-diginose, sugar components of decilorubicin.

Sir: Decilorubicin,l) a new anthracycline antibiotic produced by Streptomyces virginiae MF-266-g4 yields three kinds of sugars on hydrolysis. As reported in a previous paper,') hydrogenolysis of decilorubicin methyl ester gave rhodosamine. Two other sugar components have been obtained as their methyl glycosides by methanolysis of decilorubicin. One of them, a new nitro sugar is named decilonitrose. In this communication their structures and syntheses are reported. Methanolysis of decilorubicin (2.0 g) in 0.5 M methanolic HC1 (200 ml) at 70°C for 4.5 hours followed by column chromatography on silica gel developed with mixtures of 50: 1, 30: 1, and 6: 1 of toluene and ethyl acetate, successively, gave three methyl glycosides as colorless syrupy solids: a new nitro sugar, methyl (3-decilonitroside [1, 28 mg, easily sublimes under a reduced pressure, [a]D -13° (c 0.2, chloroform), IR: 1540 cm-1 (NO2); MS: m/z 159 (M-NO,)], methyl 4-O-succinyl-a-L-diginoside methyl ester [2, 127 mg, [a]D -129° (c 1.0, chloroform)] and the Sanomer of 2 [3, 37 mg, [a]D-0.1° (c 0.1, chloroform)]. The 1H NMR chemical shifts of 1 and 13C NMR chemical shifts of 1, 2 and 3 are shown in Tables 1 and 2, respectively. By spectral analysis, the structure of 1 was suggested to be methyl 2,3,6-trideoxy-3-C-methyl-