75712-56-0Relevant academic research and scientific papers
Formal syntheses of N-trifluoroacetyl-L-acosamine and N-trifluoroacetyl-L-daunosamine from an achiral precursor, methyl sorbate
Nagumo,Umezawa,Akiyama,Akita
, p. 171 - 173 (1995)
N-Trifluoroacetyl-L-acosamine 20 and N-trifluoroacetyl-L-daunosamine 21 were formally synthesized from an achiral precursor, methyl sorbate 4, based on enzymatic chiral induction and diastereoselective 1,4-conjugated addition of benzylamine to the olefini
Chemoenzymatic 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
Saotome, Chikako,Ono, Machiko,Akita, Hiroyuki
, p. 4137 - 4151 (2007/10/03)
A conjugated addition of benzylamine to methyl (4R,5S)-4,5-(isopropylidenedioxy)-(2E)-hexenoate 8a followed by lactonization under acidic condition proceeds to the formal total syntheses of L-daunosamine 4 and L-acosamine 2. On the other hand, direct conjugated addition of benzylamine to methyl (4S,5S)-4,5-epoxy-(2E)-hexenoate 5 and the subsequent intramolecular nucleophilic attack by the ester carbonyl group on the epoxy ring of the substrates leads to the formal total syntheses of D-acosamine 2 and D-ristosamine 1. Copyright (C) 2000 Elsevier Science Ltd.
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).
DIASTEREOSELECTIVE SYNTHESIS OF N-ACETYL-D,L-ACOSAMINE AND N-BENZOYL-D,L-RISTOSAMINE
Hirama, Masahiro,Shigemoto, Takeo,Yamazaki, Yutaka,Ito, Sho
, p. 4133 - 4136 (2007/10/02)
N-Acyl derivatives of D,L-acosamine and D,L-ristosamine were synthesized with high stereoselectivity utilizing intramolecular Michael addition of γ- and δ-carbamoyloxy-α,β-unsaturated esters.
A Brief Total Synthesis of N-Benzoyl-D,L-daunosamine
Hauser, Frank M.,Rhee, Richard P.
, p. 227 - 228 (2007/10/02)
A brief regioselective total synthesis of N-benzoyl-D,L-daunosamine from chlorosulfonyl isocyanate (2) and (E)-1,3-pentadiene (1) is described.
Synthesis of N-Trifluoroacetyl-L-acosamine and -L-daunosamine
Fronza, Giovanni,Fuganti, Claudio,Grasselli, Piero
, p. 442 - 444 (2007/10/02)
N-Trifluoroacetyl-L-acosamine (18) has been chirally synthesised from the chiral educt (1) obtained from cinnamaldehyde and bakers' yeast, whereas N-trifluoroacetyl-L-daunosamine (17) was obtained by inverting the configuration at C-4 of the intermediate
