Regioselective synthesis of 4azido-Neu2en5,7Ac(2)1Me and its intramolecular transformation to 4azido-Neu2en5,9Ac(2)1Me.

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Zhao Q, Lou Y, Xiong R, Li H, Shen J

Carbohydr Res 343 (14) 2459-2462 [2008-09-22; online 2008-06-20]

Methyl 5-N-acetyl-7-O-acetyl-4-azido-2,3-didehydro-2,4-dideoxy-neuraminic acid (4azido-Neu2en5,7 Ac(2)1Me) was synthesized regioselectively starting from 4azido-Neu2en5Ac1Me in high yield. The transformation of 4azido-Neu2en5,7Ac(2)1Me to the corresponding thermodynamically stable 4azido-Neu2en5,9Ac(2)1Me via intramolecular acetyl migration was confirmed by single-crystal X-ray diffraction analysis. The proposed rearrangement mechanism is discussed.

Ruisheng Xiong

SciLifeLab Fellow

PubMed 18635158

DOI 10.1016/j.carres.2008.06.016

Crossref 10.1016/j.carres.2008.06.016

pii: S0008-6215(08)00333-9