TY - JOUR
T1 - Syntheses of branched non-1-ynitols by chemoselective addition of (trimethylsilyl)-propargylmagnesium bromide at the anomeric center of side chain halogeno functionalized carbohydrates
AU - Vernekar, Sanjeev Kumar V.
AU - Kipke, Paul
AU - Redlich, Hartmut
PY - 2008/1
Y1 - 2008/1
N2 - A convenient method for the syntheses of non-1-ynitols 8a-8d, by chemoselective addition of (trimethylsilyl)-propargylmagnesium bromide at the anomeric center of a 1-unprotected sugar, in the presence of 3-C′-halide and 3-C′-silyl functions in the side chain is described. In addition, an efficient method for the synthesis of 3-C′-hydroxymethyl sugar 3 via the addition of C1 silyl Grignard reagents to ulose 1 and subsequent oxidation by the Fleming-Tamao method in excellent yields is reported. Also, a suitable acid-catalyzed isomerization of the 1,2-O-isopropylidene group to the 2,3-O-isopropylidene group (5a-5f), to get access to the anomeric center, in good to excellent yields has been depicted.
AB - A convenient method for the syntheses of non-1-ynitols 8a-8d, by chemoselective addition of (trimethylsilyl)-propargylmagnesium bromide at the anomeric center of a 1-unprotected sugar, in the presence of 3-C′-halide and 3-C′-silyl functions in the side chain is described. In addition, an efficient method for the synthesis of 3-C′-hydroxymethyl sugar 3 via the addition of C1 silyl Grignard reagents to ulose 1 and subsequent oxidation by the Fleming-Tamao method in excellent yields is reported. Also, a suitable acid-catalyzed isomerization of the 1,2-O-isopropylidene group to the 2,3-O-isopropylidene group (5a-5f), to get access to the anomeric center, in good to excellent yields has been depicted.
KW - Alkynes
KW - Carbohydrates
KW - Grignard reaction
KW - Isomerizations
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U2 - 10.1080/07328300801991278
DO - 10.1080/07328300801991278
M3 - Article
AN - SCOPUS:45949110869
SN - 0732-8303
VL - 27
SP - 10
EP - 31
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 1
ER -