Synthesis of all configurational isomers of 1,6-anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-beta-d-hexopyranoses.
We have prepared a full series of 1,6-anhydro-2,3,4-trideoxy-4-fluoro-2,3-epimino-beta-d-hexopyranoses. The key step was the reaction of azido sulfonates possessing a free C-4 hydroxyl with DAST and subsequent LiAlH(4) reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields. A convenient synthesis of d-mannoepimine from a readily available 3-benzylamino derivative was also developed.
Karban
Jindrich
J
Institute of the Chemical Process Fundamentals of the ASCR, Praha, Czech Republic. karban@icpf.cas.cz
Sýkora
Jan
J
Kroutil
Jirí
J
Císarová
Ivana
I
Padelková
Zdenka
Z
Budesínský
Milos
M
D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D001386:Azides; D002241:Carbohydrates