17016-65-8Relevant articles and documents
Synthesis of N-Bz-protected D-daunosamine and D-Ristosamine by silica gel promoted intramolecular conjugate addition of trichloroacetimidates obtained from osmundalactone and its epimer
Matsushima, Yoshitaka,Kino, Jun
experimental part, p. 2206 - 2211 (2010/07/06)
Trichloroacetimidates prepared from osmundalactone and its epimer unexpectedly undergo intramolecular conjugate addition during silica gel chromatography to produce oxazolines in excellent yields. The novel, simple synthesis of N-Bz-protected D-daunosamin
Total syntheses of N-trifluoroacetyl-L-daunosamine, N-trifluoroacetyl-L-acosamine, N-benzoyl-D-acosamine, and N-benzoyl-D-ristosamine from an achiral precursor, methyl sorbate
Ono, Machiko,Saotome, Chikako,Akita, Hiroyuki
, p. 1257 - 1261 (2007/10/03)
A conjugated addition of benzylamine to methyl (4R,5S)-4,5-(isopropylidenedioxy)-(2E)-hexenoate (12) followed by lactonization under acidic condition proceeds formally to the total syntheses of L-daunasamine (1) and L-acosamine (2). On the other hand, direct conjugated addition of benzylamine to methyl (4S,5S)-4,5-epoxy-(2E)-hexenoate (4) and the subsequent intramolecular nucleophilic attack by ester carbonyl group against epoxy ring of the substrates leads to the formal total syntheses of D-acosamine (2) and D-ristosamine (3).
Stereochemistry of the Epoxidations of Acyclic Allylic Amides. Applications toward the Synthesis of 2,3,6-Trideoxy-3-aminohexoses
Roush, William R.,Straub, Julie A.,Brown, Richard J.
, p. 5127 - 5136 (2007/10/02)
The stereochemistry of the epoxidation of several acyclic allylic amides is described.Diastereoselectivity in the (Z)-allylic amide series (compound 1) proved to be dependent both on the amide functionality and epoxidation reagent.The threo epoxide 3 was