1300575-45-4Relevant academic research and scientific papers
Concise and highly selective asymmetric synthesis of acosamine from sorbic acid
Bagal, Sharan K.,Davies, Stephen G.,Fletcher, Ai M.,Lee, James A.,Roberts, Paul M.,Scott, Philip M.,Thomson, James E.
, p. 2216 - 2220 (2011)
Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(α- methylbenzyl)amide to tert-butyl sorbate and subsequent chemo- and diastereoselective ammonium-directed olefinic oxidation of the resultant conjugate addition product {tert-butyl (3S,αR)-3-[N-benzyl-N-(α- methylbenzyl)amino]hex-4-ene} have been used as the key steps in a concise and highly selective asymmetric synthesis of the 2,3,6-trideoxy-3-aminohexose l-acosamine. This sequence of two chemical operations allows rapid assembly of the molecular architecture and facilitates the de novo asymmetric synthesis of methyl N,O-diacetyl-α-l-acosaminide in only 7 steps from commercially available sorbic acid in 15% overall yield.
