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Elsevier, Tetrahedron, 47(65), p. 9765-9771, 2009

DOI: 10.1016/j.tet.2009.09.083

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Asymmetric syntheses of 6-deoxyfagomin, D-deoxyrhamnojirimycin, and D-rhamnono-1,5-lactam

Journal article published in 2009 by Rui Fu, 黄培强, Yu Du, Zhao-Ying Li, Wei-Xuan Xu, Pei-Qiang Huang ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

N-Allyl protected 3-O-benzyloxglutarimide 11 was synthesized as a useful variant of the chiral building block 10. This modification allowed a high-yielding deprotection of the allyl group from the lactam intermediate 14. Starting from this building block, the asymmetric syntheses of aza-sugars 6-deoxyfagomine (2), D-rhamnono-1,5-lactam (6), as well as D-deoxyrhamnojirimycin (5) have been achieved in high regio- and/or diastereo-controlled manner. (C) 2009 Elsevier Ltd. All rights reserved. ; NSFC [20832005]; NFFTBS [J0630429]