The First Synthesis of 7-(Hydroxymethyl)thiepane-3,4,5-triols from D-(-)-Quinic Acid

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Title:	The First Synthesis of 7-(Hydroxymethyl)thiepane-3,4,5-triols from D-(-)-Quinic Acid
Authors:	Shih, Tzenge-Lien;Gao, Wei-Lin
Contributors:	淡江大學化學學系
Keywords:	Glycosidase inhibitors;d-(−)-Quinic acid;Thiepanes;Thiosugars
Date:	2013-02-18
Issue Date:	2013-05-07 07:13:13 (UTC+8)
Publisher:	Kidlington: Pergamon
Abstract:	Seven thiepanes, the seven-membered-ring thiosugars, were first synthesized in 11–12 steps starting from d-(−)-quinic acid. Each thiepane is unique for its flexible conformation with a hydroxymethyl group at its C7 position. The key step was the deprotection of ether groups in compounds 7, 8, and 18–21 by 1.0 M BCl3 of CH2Cl2 solution at −78 °C to lead to the corresponding thiepanes. These target molecules all exhibited the twisted chair conformation that fully agreed with our previous report.
Relation:	Tetrahedron 69(7), pp.1897-1903
DOI:	10.1016/j.tet.2012.12.047
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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