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Synthesis of an H type 2 and a Y (Le(y)) glycoside from thioglycoside intermediates.

作者信息

Nilsson S, Lönn H, Norberg T

机构信息

Organic Synthesis Department, BioCarb AB, Lund, Sweden.

出版信息

Glycoconj J. 1989;6(1):21-34. doi: 10.1007/BF01047887.

DOI:10.1007/BF01047887
PMID:2535475
Abstract

The trisaccharide 2-(p-trifluoroacetamidophenyl)ethyl 2-acetamido-2- deoxy-4-O-[2-O-(alpha-L-fucopyranosyl)-beta-D-galactopyranosyl]-beta-D- glucopyranoside 1 and the tetrasaccharide 2-(p-trifluoroacetamidophenyl)ethyl 2-acetamido-2-deoxy-3-O-(alpha-L- fucopyranosyl)-4-O-[2-O-(alpha-L-fucopyranosyl)-beta-D-galactopyranosyl]- beta-D-glucopyranoside 2 were synthesized. Thioglycosides, suitably protected, activated directly with methyl trifluoromethanesulfonate or dimethyl(methylthio)sulfonium tetrafluoroborate or activated after bromine treatment with halophilic reagents, were used as glycosyl donors in the construction of the glycosidic linkages.

摘要

相似文献

1
Synthesis of an H type 2 and a Y (Le(y)) glycoside from thioglycoside intermediates.
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2
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引用本文的文献

1
Synthesis of the trisaccharide, 2-(p-trifluoroacetamidophenyl)ethyl O-alpha-D-galactopyranosyl-(1-4)-O-beta-D-galactopyranosyl-(1-4)-2-acet amido-2-deoxy-beta-D-glucopyranoside, corresponding to the blood group P1 determinant.
Glycoconj J. 1991 Feb;8(1):9-15. doi: 10.1007/BF00731638.

本文引用的文献

1
Synthesis of type 2 human blood-group antigenic determinants. The H, X, and Y haptens and variations of the H type 2 determinant as probes for the combining site of the lectin I of Ulex europaeus.2型人类血型抗原决定簇的合成。H、X和Y半抗原以及H2型决定簇的变体作为欧洲荆豆凝集素I结合位点的探针。
Carbohydr Res. 1982 Nov 1;109:109-42. doi: 10.1016/0008-6215(82)84034-2.
2
Synthesis of a tri- and a hepta-saccharide which contain alpha-L-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins.合成含有α-L-呋喃岩藻糖基且属于糖蛋白复合碳水化合物部分的三糖和七糖。
Carbohydr Res. 1985 Jun 15;139:105-13. doi: 10.1016/0008-6215(85)90011-4.
3
Synthesis of a dimeric Lewis X hexasaccharide derivative corresponding to a tumor-associated glycolipid.
一种与肿瘤相关糖脂相对应的二聚岩藻糖基乳糖六糖衍生物的合成。
Carbohydr Res. 1988 Nov 15;183(1):71-82. doi: 10.1016/0008-6215(88)80046-6.
4
Synthetic, conformational, and immunochemical studies of modified Lewis b and Y human blood-group determinants to serve as probes for the combining site of the lectin IV of Griffonia simplicifolia.修饰的Lewis b和Y人类血型决定簇的合成、构象及免疫化学研究，用作非洲相思子凝集素IV结合位点的探针。
Carbohydr Res. 1988 Mar 15;174:211-37. doi: 10.1016/0008-6215(88)85093-6.
5
Tumor-associated glycolipid antigens, their metabolism and organization.肿瘤相关糖脂抗原、其代谢与组织
Chem Phys Lipids. 1986 Dec 15;42(1-3):209-33. doi: 10.1016/0009-3084(86)90054-x.
6
Synthesis of blood-group substances. 6. Synthesis of O-alpha-L-fucopyranosyl-(1 leads to 2)-O-beta-D-galactopyranosyl-(1 leads to 4)-O-[alpha-L-fucopyranosyl-(1 leads to 3)]-2-acetamide-2-deoxy-alpha-D-glucopyranose, and postulated Lewis d antigenic determinant.血型物质的合成。6. O-α-L-呋喃岩藻糖基-(1→2)-O-β-D-吡喃半乳糖基-(1→4)-O-[α-L-呋喃岩藻糖基-(1→3)]-2-乙酰胺-2-脱氧-α-D-吡喃葡萄糖的合成以及假定的Lewis d抗原决定簇。
J Org Chem. 1977 Feb 18;42(4):720-4. doi: 10.1021/jo00424a032.