Tetrahedron p. 9619 - 9628 (1994)
Update date:2022-08-03
Topics:
Yoshikawa
Murakami
Yokokawa
Inoue
Kuroda
Kitagawa
Two optically active pseudo-sugars, pseudo-α-D-glucopyranose (12) and pseudo-β-D-glucopyranose (13), were synthesized from D-glucuronolactone in favorable overall yields by using a stereoselective nitromethane addition reaction and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps. Furthermore, a biologically active pseudo-aminosguar, validamine (18) was efficiently synthesized via a substitution reaction for an acetoxyl group at the β-position of nitro group in a nitrocyclitol derivative (14) which was prepared from a synthetic intermediate (9) of pseudo-d-glucopyranoses (12,13).
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