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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 42, Number 5
JKCSEZ 42(5)
October 20, 1998 

A Facile Synthesis of Ethyl 2,6-Di-O-benzyl-3-O-(3,4,5-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside and Studies on the Regioselectivity of 2,3,4-OH Groups of Galactosyl Acceptor

Ethyl 2,6-Di-O-benzyl-3-O-(3,4,5-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside의 합성법의 개발 및 갈락토스 받게의 2,3,4-OH기들의 위치 선택성에 대한 연구
Jungsoo Park, Shinsook Yoon, Mikyung Yun, Keun Ho Chun, Jeong E Nam Shin

Campylobacter jejuni 그램 음성균의 O-antigen 부위를 구성하는 반복 단위 삼탄당 합성의 주요 중간체인 이당류들을 글루코스아민 주게와 갈락토스 받게를 β(1→3) 클리코시드 결합으로 연결함으로서 합성하였댜. 이들의 합성 과정에서 갈락토스 당 부위의 2, 3, 4번 OH기들의 글루코스아민 받게에 대한 높은 위치선택성이 발견되었으며 이를 이용하여 2, 4번 OH에 대한 선택적 보호과정을 생략할 수 있었고 결과적으로 합성과정을 단축시킬 수 있었다.

O-Antigenic part of Campylobacter jejuni gram negative bacteria was reported to consist of a repeated trisaccharide unit. The disaccharides, G]cNAc-Gal derivatives, as key intermediates for the synthesis of trisaccharide repeating units were synthesized. At the β(1→3) glycoside bond formation step between 3,4,6-tri-O-acctyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl bromide and galactosyl acceptors, high regioselectivities between 2, 3, and 4-OH groups of galactosyl acceptors were found. As a result, no further selective protection steps for OH groups of galactosyl acceptors was necessary, and more effective and compact synthetic scheme was achieved.

549 - 558
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