A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine

0428290 - ÚCHP 2015 RIV DE eng J - Journal Article
Karban, Jindřich - Horník, Štěpán - Červenková Šťastná, Lucie - Sýkora, Jan
A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine.
Synlett. Roč. 25, č. 9 (2014), s. 1253-1256. ISSN 0936-5214. E-ISSN 1437-2096
Institutional support: RVO:67985858
Keywords : carbohydrates * fluorine * antitumor agents
Subject RIV: CC - Organic Chemistry
Impact factor: 2.419, year: 2014

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.
Permanent Link: http://hdl.handle.net/11104/0234623