α-Selective glycosylation with 5-thioglucopyranosyl donors; synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units
A general method for α-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue. A general method for α-selective glycosylation with 5-thiogluc...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 13; no. 6; pp. 1063 - 1066 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Oxford
Elsevier Ltd
24.03.2003
Elsevier |
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| Abstract | A general method for α-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue.
A general method for α-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. A isomaltotetraoside analogue was synthesized as the application. |
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| AbstractList | A general method for alpha-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue. A general method for α-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue. A general method for α-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. A isomaltotetraoside analogue was synthesized as the application. |
| Author | Hashimoto, Masaru Matsuda, Hiroko Ohara, Keiichiro Miyairi, Kazuo Okuno, Toshikatsu Morii, Yasuharu |
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| Cites_doi | 10.1139/v93-239 10.2174/0929867306666220207213740 10.1016/S0040-4039(00)74054-8 10.1002/anie.198602121 10.1021/jo011142u 10.1021/bi025541a 10.1042/bj3210557 10.1016/S0957-4166(00)80386-9 10.1016/S0040-4039(02)01760-4 10.1021/jo9800356 10.1016/S0040-4039(00)86974-9 |
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| References | BIB9 Witczak (BIB3) 1999; 6 Izumi, Suhara, Ichikawa (BIB12) 1998; 63 Hashimoto, Izumi (BIB13) 1993; 34 BIB16 Gurjar, Nagaprasad, Ramana (BIB5) 2002; 43 Schmidt (BIB17) 1986; 25 BIB18 Davies, Wilson, Henrissat (BIB6) 1997; 321 BIB19 Shimizu, Nakatsu, Miyairi, Okuno, Kato (BIB7) 2002; 41 Dondoni, Marra, Mizuno, Ciovannini (BIB8) 2002; 67 Mehta, Jordan, Weimar, Kreis, Batchelor, Einstein, Pinto (BIB11) 1994; 5 Oikawa, Yoshioka, Yonemitsu (BIB15) 1982; 23 Spohr, Bach, Spiro (BIB4) 1993; 71 Driguez, H., Thiem, J. Eds. Springer: Berlin, 1999. Yuasa, Hashimoto (BIB10) 1999; 19 BIB14 Gurjar (10.1016/S0960-894X(03)00072-6_BIB5) 2002; 43 Dondoni (10.1016/S0960-894X(03)00072-6_BIB8) 2002; 67 Izumi (10.1016/S0960-894X(03)00072-6_BIB12) 1998; 63 Hashimoto (10.1016/S0960-894X(03)00072-6_BIB13) 1993; 34 Oikawa (10.1016/S0960-894X(03)00072-6_BIB15) 1982; 23 Mehta (10.1016/S0960-894X(03)00072-6_BIB11) 1994; 5 Schmidt (10.1016/S0960-894X(03)00072-6_BIB17) 1986; 25 Shimizu (10.1016/S0960-894X(03)00072-6_BIB7) 2002; 41 Spohr (10.1016/S0960-894X(03)00072-6_BIB4) 1993; 71 Davies (10.1016/S0960-894X(03)00072-6_BIB6) 1997; 321 10.1016/S0960-894X(03)00072-6_BIB1 10.1016/S0960-894X(03)00072-6_BIB2 Witczak (10.1016/S0960-894X(03)00072-6_BIB3) 1999; 6 Yuasa (10.1016/S0960-894X(03)00072-6_BIB10) 1999; 19 |
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| Snippet | A general method for α-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed.... A general method for alpha-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed.... |
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| SubjectTerms | Carbohydrate Sequence Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Glucose - analogs & derivatives Glucose - chemistry Glycosylation Indicators and Reagents Models, Molecular Molecular Mimicry Molecular Sequence Data Monosaccharides - chemistry Oligosaccharides - chemistry Organic chemistry Preparations and properties |
| Title | α-Selective glycosylation with 5-thioglucopyranosyl donors; synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units |
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