TY - JOUR
T1 - Synthesis of the 3'-C-carboxymethyl Lewis X derivative
T2 - A novel selectin blocker
AU - Ishida, Hideharu
AU - Hosokawa, Hiroyuki
AU - Kondo, Hirosato
AU - Kiso, Makoto
AU - Hasegawa, Akira
N1 - Funding Information:
This work was supportedin part by Grants-in-Aid for ScientificR esearch(B ) (No. 07456162a) nd Scientific Researcho n Priority Areas (No. 05274102) from the Ministry of EducationS, ciencea nd Culture of Japan.
PY - 1997/9/5
Y1 - 1997/9/5
N2 - The 3'-C-carboxymethyl Le(x) derivative carrying the 2-(tetradecyl)hexadecyl residue was synthesized by employing 3'-C-carboxymethyl galactose as a key intermediate, which was prepared from the suitably protected galactose by Swern oxidation and Wittig-Horner carboxymethylenation, followed by stereoselective reduction of the double bond. The compound obtained showed much more potent activity as a selectin blocker than the sialyl Le(x) derivative with 2-(tetradecyl)hexadecyl residue.
AB - The 3'-C-carboxymethyl Le(x) derivative carrying the 2-(tetradecyl)hexadecyl residue was synthesized by employing 3'-C-carboxymethyl galactose as a key intermediate, which was prepared from the suitably protected galactose by Swern oxidation and Wittig-Horner carboxymethylenation, followed by stereoselective reduction of the double bond. The compound obtained showed much more potent activity as a selectin blocker than the sialyl Le(x) derivative with 2-(tetradecyl)hexadecyl residue.
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U2 - 10.1016/S0008-6215(97)00156-0
DO - 10.1016/S0008-6215(97)00156-0
M3 - Article
AN - SCOPUS:0030763192
VL - 303
SP - 131
EP - 133
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 2
ER -