TY - JOUR
T1 - Synthesis of Fluorescent 4-Methyl-7-thiocoumaryl S-Glycosides of Sialic Acid
AU - Tanaka, Makoto
AU - Kai, Toshitsugu
AU - Sun, Xue
AU - Takayanagi, Hiroaki
AU - Furuhata, Kimio
AU - Uda, Yutaka
PY - 1995/1/1
Y1 - 1995/1/1
N2 - Condensation of 4-methyl-7-thiocoumarin sodium salt with methyl (2), methyl (11), and methyl (14) under Williamson reaction conditions gave the corresponding a-glycosides in good yields. Deprotection of these a-glycosides gave three new fluorogenic substrates, the 4-methylcoumarin-7-yl S-glycosides of N-acetylneuraminic acid, N-glycolylneuraminic acid, and acid (KDN). Furthermore, we have developed a facile method for preparation of benzyl acid (7), a key intermediate for the synthesis of N-glycolylneuraminic acid. © 1995, The Pharmaceutical Society of Japan. All rights reserved.
AB - Condensation of 4-methyl-7-thiocoumarin sodium salt with methyl (2), methyl (11), and methyl (14) under Williamson reaction conditions gave the corresponding a-glycosides in good yields. Deprotection of these a-glycosides gave three new fluorogenic substrates, the 4-methylcoumarin-7-yl S-glycosides of N-acetylneuraminic acid, N-glycolylneuraminic acid, and acid (KDN). Furthermore, we have developed a facile method for preparation of benzyl acid (7), a key intermediate for the synthesis of N-glycolylneuraminic acid. © 1995, The Pharmaceutical Society of Japan. All rights reserved.
KW - 7-mercapto-4-methylcoumarin
KW - fluorogenic substrate
KW - KDN sialic acid
KW - N-acetylneuraminic acid
KW - N-glycolylneuraminic acid
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U2 - 10.1248/cpb.43.1844
DO - 10.1248/cpb.43.1844
M3 - Article
SN - 0009-2363
VL - 43
SP - 1844
EP - 1848
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 11
ER -