Stereoselective synthesis of several azido/amino- and diazido/diamino-myo-inositols and their phosphates from p-benzoquinone.
A practical route is described for the preparation of azido-myo-inositols, amino-myo-inositols and azido-conduritol B derivatives. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol B derivative. Selective introduction of nitrogen-containing functional groups in four of the six possible positions in the cyclitol moiety is followed by further functionalization to yield the target compounds.
Podeschwa
Michael A L
MA
Institut für Organische Chemie, Bergische Universität Wuppertal, Gaussstrasse 20, 42097 Wuppertal, Germany.
Plettenburg
Oliver
O
Altenbach
Hans-Josef
HJ
D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D016227:Benzoquinones / Q000737:chemistry*; D003511:Cyclohexanols / Q000737:chemistry; D053138:Cyclohexenes; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D007295:Inositol Phosphates / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D001386:Azides; D016227:Benzoquinones; D003511:Cyclohexanols; D053138:Cyclohexenes; D007295:Inositol Phosphates; C004532:quinone; C090988:conduritol B; D007294:Inositol