A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxy gulopyranoside and epi-tolyposamine

Article abstract of DOI:10.1016/S0040-4020(97)00304-9

New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported.