42491-79-2Relevant articles and documents
Organocatalytic syn-aldol reactions of dioxanones with (S)-isoserinal hydrate: Synthesis of L-deoxymannojirimycin and L-deoxyidonojirimycin
Palyam, Nagarjuna,Majewski, Marek
supporting information; experimental part, p. 4390 - 4392 (2009/09/06)
(Chemical Equation Presented) We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2
New convenient reagents for chemoselective N-alkoxycarbonylation of (S)-isoserine: Application in the isepamicin synthesis
Doktorov, Konstantin,Tarpanov, Velichko,Mechkarova, Pepa
, p. 3709 - 3718 (2008/02/10)
A synthesis of a series of N-alkoxycarbonyl mercaptobenzothiazoles (MBTs) and their application as reagents for chemoselective protection of amino group are presented herein. It was shown that all new reagents, Z-MBT, Fmoc-MBT, Phoc-MBT, and Tec-MBT, are highly effective in the selective N-alkoxycarbonylation of (S)-isoserine. The transformation is a simple, fast, and low-cost protocol, which is applicable in scale-up experiments. The starting MBT was fully recovered at the end of the process, which is an additional advantage of the method. The efficiency of the Z-reagent was also demonstrated by the selective protection of both gentamicin B and (S)-isoserine before their peptide-type coupling in the synthesis of the aminoglycoside antibiotic isepamicin. Copyright Taylor & Francis Group, LLC.
Efficient synthesis of N-benzyloxycarbonyl- and N-tert-butoxycarbonyl-(S)-isoserine and their derivatives
Andruszkiewicz, Ryszard,Wyszogrodzka, Monika
, p. 2101 - 2103 (2007/10/03)
A mild and efficient synthesis of N-protected (S)-isoserine from (S)-malic acid monoester via an oxazolidin-2-one is described.
