133870-87-8Relevant academic research and scientific papers
Stereoselective synthesis of 3-amino-4,5-dihydroxyaldehydes - A novel preparation of N-acetyl-L-daunosamine
Effenberger, Franz,Roos, Juergen
, p. 1085 - 1095 (2000)
A general route for the stereoselective synthesis of 3-amino-4,5-dihydroxyaldehydes, with almost any desired configuration at the three stereogenic centers, is described by applying a combination of enzymatic and chemical steps. L-Daunosamine 1, for example, the glycosidic fragment of many important anthracycline antibiotics has been prepared by this route starting from O-allyl-L-lactaldehyde (S)-6a. (R)-Hydroxynitrile lyase (HNL) catalyzed addition of HCN to (S)-6a yields the 2,3-dihydroxynitrile (2S,3S)-7a with high stereoselectivity (91% de) in 75% yield. The addition of allyl Grignard to the O-protected 2,3-dihydroxynitrile (2S,3S)-9a and subsequent hydrogenation of the imino intermediate leads to 4-amino-2,3-dihydroxy-1-heptene (4S,5S,6S)-12a, which after ozonization and deprotection gives N-acetylated L-daunosamine 14a in a total yield of 15% referring to (S)-6a. The general applicability of this chemoenzymatic multistep procedure is demonstrated in the stereoselective synthesis of the unnatural aminodeoxy sugar (2S,3S,4S)-14b, starting from isovaleraldehyde 3. Copyright (C) 2000 Elsevier Science Ltd.
A convenient preparation of 2-substituted (S)-aziridines
Effenberger,Stelzer
, p. 283 - 286 (2007/10/02)
2-Monosubstituted (S)-aziridines (S)-3 were obtained by hydrogenation of (R)-2-sulfonyloxynitriles (R)-2 with LiAlH4 in good chemical yields and high enantiomeric excess.
Enzyme-Catalyzed Reactions, 15. - Preparation of (R)-2-(Sulfonyloxy)nitriles and their Reactions with Acetates - Inversion of the Configuration of Optically Active Cyanohydrins
Effenberger, Franz,Stelzer, Uwe
, p. 779 - 786 (2007/10/02)
2-(Sulfonyloxy)nitriles (R)-6,7,8 are obtained in high optical purity from the respective cyanohydrins (R)-2 by sulfonylation with methanesulfonyl chloride (3), toluenesulfonyl chloride (4), and trifluoromethanesulfonic anhydride (5), respectively.In cont
