2880-95-7Relevant academic research and scientific papers
Synthesis of higher 3-deoxy-2-ketoaldonic acids by construction and deoximation of their hydroxyiminoesters
Mikshiev,Kornilov,Paidak,Zhdanov
, p. 476 - 482 (2007/10/03)
The synthesis of natural 3-deoxy-2-keto-D-arabino-heptonic and 3-deoxy-2-keto-D-manno-octonic acids is reported, involving preparation of polyalkyl malonates and higher hydroxyiminoester derivatives of the target acids, followed by deoximation of the latter with nitrosylsulfuric acid, hydrolysis of the protective groups, and identification of the acids as their methyl ester methyl glycoside or ammonium salt. A mixture of products of acidic C-nitrosation of 2-hydroxycarbonyl-2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-manno-octono-1,4-lac tone was characterized in a similar way. Three procedures for deoximation of the key oximes with nitrosylsulfuric acid in ether, as well as in acetic and formic acids were proposed.
The first synthesis of the ketene dithioacetals from sugar lactones: A convenient access to 3-ulosonic acids
Mlynarski, Jacek,Banaszek, Anna
, p. 5425 - 5428 (2007/10/03)
Isomeric 2-deoxy aldonolactones undergo Horner-Emmons reactions with 2- [bis(2,2,2-trifluoroethoxy)phosphoryl]1,3-dithiane, to give the corresponding ketene dithioacetals, which are the key intermediates in the synthesis of 3- deoxy-2-keto-aldonic acids.
A novel chemical synthesis of a 3-deoxy-D-arabino-heptulosonic acid 7-phosphate (DAHP) derivative and its 2-deoxy analogue
Mlynarski, Jacek,Banaszek, Anna
, p. 69 - 75 (2007/10/03)
Using 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl cyanide as a precursor, methyl (methyl 3-deoxy-α-D-arabino-hept-2-ulopyranosid)onate (6) and its 2-deoxy analogue (10) were prepared. The synthesis involved an elimination of one molecule of acetic acid from C-2-C-3 and transformation of the CN group into COOMe, followed by methoxymercuration with subsequent reductive removal of the mercuri residue to give 6 or hydrogenation of the double bond to give 10. Phosphorylation of the 7-OH group led to the title compounds.
Synthesis of 4-amino-3,4-dideoxy-D-arabino-heptulosonic acid 7-phosphate, the biosynthetic precursor of C7N units in ansamycin antibiotics
Kirschning, Andreas,Bergon, Philippe,Wang, Jeh-Jeng,Breazeale, Steven,Floss, Heinz G.
, p. 245 - 256 (2007/10/02)
The synthesis of 4-amino-3,4-dideoxy-D-arabino-heptulosonic acid 7-phosphate (15), the first committed intermediate in a new branch of the shikimate pathway of aromatic biosynthesis, is reported from 2-deoxy-D-glucose in 14 steps in 10-12percent overall y
Determination of the Anomeric Configuration in Glycosides of 3-Deoxy-2-aldulosonic Acids by Circular Dichroism and X-Ray Crystallography
Charon, Daniel,Szabo, Ladislas,Cesario, Michele,Guilhem, Jean
, p. 3055 - 3064 (2007/10/02)
Methyl (methyl 3-deoxy-D-arabino-2-heptulopyranosid)onate was obtained by acid-catalysed esterification and glycosidation of the free 2-aldulosonic acid.The molecular geometry of the glycosidic ester was determined by X-ray crystallography, and indicated both that the molecule was α-anomer and that the ring oxygen and the carboxy-group were nearly coplanar.The c.d. spectrum showed a negative n -> ?* transition band centred at 224 nm.The c.d. spectra od a number of methyl glycopyranosides derived from 6-, 7-, and 8-carbon 3-deoxy-2-aldulosonic acids demonstrated that all the compounds believed to be α-glycosides had negative maxima, and all those believed to be β-glycosides had positive maxima around 220 nm independent of their 2C5 or5C2 conformation.The only known furanoside, believed to be a β-anomer, also had a positive maximum.The chirality of the anomeric carbon atom of this class of compound can thus be conveniently established by determining the sign of the Cotton effect at 220 nm.
