Tetrahedron Letters p. 5477 - 5480 (1989)
Update date:2022-08-04
Topics: Purification Protection of Functional Groups Starting Material Analysis and Characterization Ring Formation De-Protection Functional Group Modification
Klein, P.A.M. van der
Boons, G.J.P.H.
Veeneman, G.A.
Marel, G.A. van der
Boom, J.H. van
Treatment of 2,3:5,6-di-O-isopropylidene-D-mannitol with thionyl chloride followed by oxidation gave the corresponding 1,4-cyclic sulfate.Ring opening of the cyclic sulfate with the anion of ethyl 1,3-dithiane-2-carboxylate, and subsequent acidolysis and unmasking of the thioketal, afforded ethyl 4,5:7,8-di-O-isopropylidene-3-deoxy-α(β)-D-manno-2-octulosonate in an excellent yield.
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