T. Hanaya, K. Ohmori, H. Yamamoto
Apr 1, 1990
Citations
0
Influential Citations
14
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Methyl 5,6-dideoxy-2,3-O-isopropylidene-6-nitro-α-D-lyxo-hex-5-enofuranoside (10) was prepared from D-mannose in 7 steps. Addition of methyl methylphosphinate to 10, followed by the catalytic hydrogenation and diazotization, afforded methyl 5-deoxy-2,3-O-isopropylidene-5-[(methoxy)methylphosphinyl]-α-D-lyxo-hexofuranoside, which was then converted into 6-O-triphenylmethyl and 6-O-tetrahydropyranyl derivatives (14, 15). By reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by acid hydrolysis, both 14 and 15 provided the D-mannopyranoses (together with a minor proportion of L-gulopyranoses) having a methylphosphinylidene group in place of the ring oxygen. These were converted into 1,2,3,4,6-penta-O-acetyl derivatives, whose structures and conformations were established by spectroscopy.