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KMID : 1059519980420050549
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Journal of the Korean Chemical Society
1998 Volume.42 No. 5 p.549 ~ p.558
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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
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Park Jung-Soo
Yoon Shin-Sook
Yun Mi-Kyung
Chun Keun-Ho
Nam Jeong-E
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Abstract
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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.
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KEYWORD
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