STEREOSELECTIVE CONVERSION OF D-GLUCURONOLACTONE INTO PSEUDO-SUGAR - SYNTHESES OF PSEUDO-ALPHA-D-GLUCOPYRANOSE, PSEUDO-BETA-D-GLUCOPYRANOSE, AND VALIDAMINE
M. Yoshikawa et al., STEREOSELECTIVE CONVERSION OF D-GLUCURONOLACTONE INTO PSEUDO-SUGAR - SYNTHESES OF PSEUDO-ALPHA-D-GLUCOPYRANOSE, PSEUDO-BETA-D-GLUCOPYRANOSE, AND VALIDAMINE, Tetrahedron, 50(32), 1994, pp. 9619-9628
Two optically active pseudo-sugars, pseudo-alpha-D-glucopyranose (12)
and pseudo-beta-D-glucopyranose (13), were synthesized from D-glucuron
olactone in favorable overall yields by using a stereoselective nitrom
ethane addition reaction and a reductive elimination of an ethoxyethox
yl moiety with NaBH4 as key steps. Furthermore, a biologically active
pseudo-aminosugar, validamine (18) was efficiently synthesized via a s
ubstitution reaction for an acetoxyl group at the beta-position of nit
ro group in a nitrocyclitol derivative (14) which was prepared from a
synthetic intermediate (9) of pseudo-D-glucopyranoses (12, 13).