STEREOSELECTIVE PREPARATION OF SYNTHETIC EQUIVALENTS OF 2-DEOXY-2-AMINO- AND 3-DEOXY-3-AMINOTETROSES FROM MALIC ACID. APPLICATION TO THE SYNTHESIS OF C18-D-RIBO-PHYTOSPHINGOSINE

Article abstract of DOI:10.1016/S0040-4039(01)80606-7

"Electrophilic amination" of β-hydroxyester 5, derived from (S)malic acid, with di-t-butylazodicarboxylate allowed preparation of new synthetic equivalents of 2-deoxy-2-amino- and 3-deoxy-3-amino-tetroses.As an application, D-ribo-C₁₈-phytosphingosine was stereoselectively synthesized.