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A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine
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SYSNO ASEP 0428290 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine Author(s) Karban, Jindřich (UCHP-M) RID, ORCID, SAI
Horník, Štěpán (UCHP-M) ORCID, RID, SAI
Červenková Šťastná, Lucie (UCHP-M) RID, ORCID, SAI
Sýkora, Jan (UCHP-M) RID, ORCID, SAISource Title Synlett. - : Georg Thieme Verlag - ISSN 0936-5214
Roč. 25, č. 9 (2014), s. 1253-1256Number of pages 4 s. Language eng - English Country DE - Germany Keywords carbohydrates ; fluorine ; antitumor agents Subject RIV CC - Organic Chemistry Institutional support UCHP-M - RVO:67985858 UT WOS 000337238300007 DOI 10.1055/s-0033-1341187 Annotation Peracetylated 3-deoxy-3-fluoro analogues of D-glucosamine and D-galactosamine 3 and 4, respectively, were prepared from 1,6:2,3-dianhydro-4-O-benzyl-β-D-mannopyranose (6). Azidolysis of 6 followed by reaction with diethylaminosulfur trifluoride gave 1,6-anhydro-2-azido-4-O-benzyl-2,3-dideoxy-3-fluoro- β-D-glucopyranose (9). Cleavage of the internal acetal, hydrogenation and acetylation yielded 3. De-O-benzylation of 9 followed by a configurational inversion at C4 gave 1,6-anhydro-2-azido-2,3-dideoxy- 3-fluoro-β-D-galactopyranose (18), which provided 4 after cleavage of the 1,6-anhydro bridge, reduction, and acetylation. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2015
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