Synthesis of the amino sugar from C-1027.
[reaction: see text] The amino sugar side chain (2) from C-1027Chr was synthesized in 12 steps from mannose. The key reactions are an internal displacement by nitrogen to introduce the cis amino group at C-4 and the methylation of an enolate at C-5.
Semmelhack
M F
MF
Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA. mfshack@princeton.edu
Jiang
Y
Y
Ho
D
D
D000606:Amino Sugars / Q000138:chemical synthesis*; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D053281:Enediynes; D008358:Mannose / Q000737:chemistry
D000606:Amino Sugars; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D053281:Enediynes; C058024:C 1027; D008358:Mannose