Structural Elucidation of a Hydrolysis Product from Derivatives of Allofuranose

doi:10.11938/cjmr20170207

Abstract

Abstract: 1,2-O-(1-methylethylidene)-3-C-methylnitro-α-D-allofuranose (2) was obtained through selective deprotection of 1,2;5,6-Di-O-isproplidene-3-C-methylnitro-α-D-allofuranose (1) under an acidic condition. C-3 nitrostyrenes (3) was synthetized through Moffatt dehydration from compound 1 under an acidic condition. A hydrolysis product 1,2-O-(1-methylethylidene)-3-C-methylnitro-α-D-glocufuranose (2') which had a reversed C-3 configuration was obtained by an unexpected oxa Michael addition. Compounds 2 and 2' were C-3 diasteroisomers. Compound 2' was characterized with NMR spectroscopy techniques, including ¹H NMR, ¹³C NMR, DEPT-135, ¹H-¹H COSY, gHSQC and gHMBC. ¹H and ¹³C chemical shifts of compound 2' were also fully assigned. The molecular structure of compound 2' was determined.

Key words: nuclear magnetic resonance (NMR), assignment, 2D NMR, hydrolysis product

CLC Number:

ZHANG En, CUI De-yun, SUN Wei, LI Peng-yun, XU Jin-mei, LIU Hong-min. Structural Elucidation of a Hydrolysis Product from Derivatives of Allofuranose[J]. Chinese Journal of Magnetic Resonance, 2017, 34(2): 183-190.

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