Catalytic regioselective oxidation of glycosides.

نویسندگان

  • Manuel Jäger
  • Marcel Hartmann
  • Johannes G de Vries
  • Adriaan J Minnaard
چکیده

Discrimination among equals: A catalytic method for the selective oxidation of unprotected glycosides, both monosaccharides and disaccharides, has been developed. The resulting ketosaccharides are isolated in moderate to excellent yields. This approach provides a basis for protecting-group-free synthetic transformations of carbohydrates.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Magnesium Oxide Nanoparticles for Catalytic Synthesis of 2-Substituted Alcohols from Regioselective Ring Opening of Epoxides in Water

Epoxides undergo regioselective ring opening with various nucleophiles using catalytic amount of nano magnesium oxide and water as solvent under mild reaction conditions. The remarkable features of this method are improved yields, high regioselectivity, and green chemistry agreement.

متن کامل

Novel pH-Stable Glycoside Hydrolase Family 3 β-Xylosidase from Talaromyces amestolkiae: an Enzyme Displaying Regioselective Transxylosylation.

This paper reports on a novel β-xylosidase from the hemicellulolytic fungus Talaromyces amestolkiae. The expression of this enzyme, called BxTW1, could be induced by beechwood xylan and was purified as a glycoprotein from culture supernatants. We characterized the gene encoding this enzyme as an intronless gene belonging to the glycoside hydrolase gene family 3 (GH3). BxTW1 exhibited transxylos...

متن کامل

IBS-catalyzed regioselective oxidation of phenols to 1,2-quinones with Oxone®.

We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone® as a co-oxidant under mild conditions. The reaction rate of I...

متن کامل

Regioselective Carbohydrate Oxidations: A Nuclear Magnetic Resonance (NMR) Study on Selectivity, Rate, and Side-Product Formation

Palladium/neocuproine catalyzed oxidation of glucosides shows an excellent selectivity for the C3-OH, but in mannosides and galactosides, unselective oxidation was initially observed. For further application in more-complex (oligo)saccharides, a better understanding of the reaction, in terms of selectivity and reactivity, is required. Therefore, a panel of different glycosides was synthesized, ...

متن کامل

The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution.

The structure of human P450 2C9 complexed with flurbiprofen was determined to 2.0 A by x-ray crystallography. In contrast to other structurally characterized P450 2C enzymes, 2C5, 2C8, and a 2C9 chimera, the native catalytic domain of P450 2C9 differs significantly in the conformation of the helix F to helix G region and exhibits an extra turn at the N terminus of helix A. In addition, a distin...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Angewandte Chemie

دوره 52 30  شماره 

صفحات  -

تاریخ انتشار 2013