About: A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine     Goto   Sponge   NotDistinct   Permalink

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  • 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.
  • 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. (en)
Title
  • A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine
  • A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine (en)
skos:prefLabel
  • A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine
  • A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine (en)
skos:notation
  • RIV/67985858:_____/14:00428290!RIV15-AV0-67985858
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  • RIV/67985858:_____/14:00428290
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  • carbohydrates; fluorine; antitumor agents (en)
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  • DE - Spolková republika Německo
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  • 25
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  • Sýkora, Jan
  • Karban, Jindřich
  • Červenková Šťastná, Lucie
  • Horník, Štěpán
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  • 000337238300007
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  • 0936-5214
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  • 10.1055/s-0033-1341187
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