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Synthesis 1991; 1991(5): 347-349
DOI: 10.1055/s-1991-26461
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Synthesis of 2,3,5-Tri-O-benzyl-D-arabinitol 1,4-Cyclic Sulfate and Its Conversion into Potential Precursors of Shikimate Substrate Analogues

Pieter A. M. van der Klein* , Arjan E. J. de Nooy, Gijs A. van der Marel, Jacques H. van Boom
  • *Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands
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Publication Date:
29 April 2002 (online)

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A practical route to deoxycarbohydrates, which may serve as starting materials in the synthesis of shikimate substrate analogues is described. The deoxy derivatives ethyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-arabino-2 -heptulopyranosonate (10), 3,4,6-tri-O-benzyl-2-deoxy-α/β-D -arabino-hexopyranose (11) and 3,4,6-tri-O-benzyl-2-deoxy-D -arabino-hexono-1,5-lactone (12) were prepared from 2,3,5-tri-O-benzyl-D-arabinitol 1,4-sulfate (3b) by regioselective nucleophilic ring opening with 2-ethoxycarbonyl-2-lithio-1,3-dithiane (4), bis(methylthio)methyllithium (5), and tris(methylthio)methyllithium (6), respectively, followed by consecutive hydrolysis of the resulting sulfates and unmasking of the alkylthio functions.