Tetrahedron letters

Diastereoselective hydrogenations of α-(2′, 3′, 4′, 6′-tetra-O-acetyl-β-d-glucopyranosyloxymethylene) carboxylic esters: A route to stereopure aldol derivatives

DS Larsen, A Schofield, RJ Stoodley, PD Tiffin

文献索引：Larsen, David S.; Schoffeld, Anthony; Stoodley, Richard J.; Tiffin, Peter D. Tetrahedron Letters, 1994 , vol. 35, # 49 p. 9285 - 9288

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被引用次数: 7

摘要

The stereostructures of the dihydro derivatives 50 and 6a were established by synthesis (Scheme 2). Thus, in the presence of silver (I) carbonate, the acetobromoglucose 11* O underwent condensation with methyl (s)-3-hydroxy-2-methylpropanoate 12 to give the glucoside Sag (40% yield after chromatography and crystallisation), mp 67-69 “C,[a] D-14 (c 0.3, CH2CI2). and with methyl (R)-3-hydroxy-ZmethyIpropanorJe 13 to afford the ...