Synthesis of the 3'-C-carboxymethyl Lewis X derivative: A novel selectin blocker

Hideharu Ishida; Hiroyuki Hosokawa; Hirosato Kondo; Makoto Kiso; Akira Hasegawa

doi:10.1016/S0008-6215(97)00156-0

Synthesis of the 3'-C-carboxymethyl Lewis X derivative: A novel selectin blocker

Hideharu Ishida, Hiroyuki Hosokawa, Hirosato Kondo, Makoto Kiso, Akira Hasegawa

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	131-133
Number of pages	3
Journal	Carbohydrate Research
Volume	303
Issue number	2
DOIs	https://doi.org/10.1016/S0008-6215(97)00156-0
Publication status	Published - Sep 5 1997
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Biochemistry
Organic Chemistry

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title = "Synthesis of the 3'-C-carboxymethyl Lewis X derivative: A novel selectin blocker",

abstract = "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.",

author = "Hideharu Ishida and Hiroyuki Hosokawa and Hirosato Kondo and Makoto Kiso and Akira Hasegawa",

year = "1997",

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language = "English",

volume = "303",

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journal = "Carbohydrate Research",

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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

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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DO - 10.1016/S0008-6215(97)00156-0

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JO - Carbohydrate Research

JF - Carbohydrate Research

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