1300575-46-5

Upstream product

• 184840-85-5 tert-Butyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate 
• 178976-42-6 Methyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate 
• 81838-85-9 tert-butyl (2E,4E)-2,4-hexadienoate 
• 100-52-7 benzaldehyde 
• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 1300575-45-4 C₂₂H₂₇NO₃ 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 110-44-1 sorbic Acid 

Relevant academic research and scientific papers

Concise and highly selective asymmetric synthesis of acosamine from sorbic acid

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.