TY - JOUR
T1 - Synthesis of 3-deoxyaldulosonic acid esters by one-carbon chain extension of glycal-derived lactone precursors
AU - Horton, Derek
AU - Issa, Mohamady
AU - Priebe, Waldemar
AU - Sznaidman, Marcos L.
N1 - Funding Information:
This work was supported, in part, by NIH grant No. NIGMS-11976.
PY - 1993/8/17
Y1 - 1993/8/17
N2 - A convenient preparative route is described for 3-deoxyaldulosonic acids. Glycal precursors are oxidatively converted into 2-deoxyaldonolactones, which react with 1,3-dithian-2-yl anion to afford 1,3-propanediyl dithioacetals of higher 3-deoxyaldosuloses. Deprotection with mercuric salts in wet or dry alcohols gave high yields of the corresponding alkyl aldulosonates. Preparative reaction conditions were optimized and the anomeric configurations of teh ketopyranose products were established b 13C NMR.
AB - A convenient preparative route is described for 3-deoxyaldulosonic acids. Glycal precursors are oxidatively converted into 2-deoxyaldonolactones, which react with 1,3-dithian-2-yl anion to afford 1,3-propanediyl dithioacetals of higher 3-deoxyaldosuloses. Deprotection with mercuric salts in wet or dry alcohols gave high yields of the corresponding alkyl aldulosonates. Preparative reaction conditions were optimized and the anomeric configurations of teh ketopyranose products were established b 13C NMR.
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U2 - 10.1016/0008-6215(93)84027-4
DO - 10.1016/0008-6215(93)84027-4
M3 - Article
C2 - 8370034
AN - SCOPUS:0027642092
SN - 0008-6215
VL - 246
SP - 105
EP - 118
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1
ER -