6730-18-3Relevant academic research and scientific papers
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer
Carrau, Gonzalo,Bellomo, Ana Inés,Suescun, Leopoldo,Gonzalez, David
, p. 788 - 802 (2019/01/08)
This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, pro-tection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods.
Stereoselective synthesis of several azido/amino- and diazido/diamino-myo-inositols and their phosphates from p-benzoquinone
Podeschwa, Michael A.L.,Plettenburg, Oliver,Altenbach, Hans-Josef
, p. 1919 - 1929 (2007/10/03)
A practical route is described for the preparation of azido-myo-inositols, amino-myo-inositols and azido-conduritol B derivatives. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol B derivative. Selective introduction of nitrogen-containing functional groups in four of the six possible positions in the cyclitol moiety is followed by further functionalization to yield the target compounds.
Convenient access to both enantiomers of new azido- and aminoinositols via a chemoenzymatic route
Sanfilippo, Claudia,Patti, Angela,Piattelli, Mario,Nicolosi, Giovanni
, p. 2809 - 2817 (2007/10/03)
1,2-diacetylconduritol E, (±)-1, through complementary use of Mucor miehei (Lipozyme IM) and Candida cylindracea lipases, affords (1S)-1,2- diacetylconduritol E, (+)-1, (1R)-1,2-diacetylconduritol E, (-)-1, (1S)- 1,2,4-triacetylconduritol E, (+)-2, (1R)-1
Total Synthesis of Methoxyhygromycin and Its 5-Epimer
Chida, Noritaka,Nakazawa, Keiichi,Ohtsuka, Masami,Suzuki, Minoru,Ogawa, Seiichiro
, p. 423 - 426 (2007/10/02)
Methoxyhygromycin, an antibiotic having a unique structure among the aminocyclitol antibiotics, and its 5-epimer are first synthesized.This synthesis fully confirmed the proposed structure of the antibiotic and revealed that neo-configuration of cyclitol
Cyclitol Reactions, XII. - Enantioselective Synthesis of the Central Pseudodisaccharide Unit of α-Glycosidase Inhibitors of the Oligostatine Type
Paulsen, Hans,Roeben, Wolfgang
, p. 974 - 994 (2007/10/02)
A pseudodisaccharide unit of the α-glycosidase inhibitors of the oligostatine type has been synthesized.At first a synthesis of the enantiomeric pure derivative of the branched amino inositol 26 has been developed.A linkage of 26 with the reactive epoxide
