BIOMAT Database Logo BIOMAT Database Logo

A short and highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides. 2011

Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

A highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides via BF(3)·OEt(2) promoted tandem hydroamination/glycosylation of 3,4-di-O-acetyl-6-deoxy-L-glucal and L-galactal has been developed. The new method proceeds in a completely stereocontrolled manner within a short reaction time. Preparation of a library of L-ristosamine and L-epi-daunosamine glycosides with potential biochemical applications, by varying each component, exemplified the generality of the reaction.

UI MeSH Term Description Entries
D005690 Galactose An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (GALACTOSE-1-PHOSPHATE URIDYL-TRANSFERASE DEFICIENCY DISEASE) causes an error in galactose metabolism called GALACTOSEMIA, resulting in elevations of galactose in the blood. D-Galactose,Galactopyranose,Galactopyranoside,D Galactose
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
D006595 Hexosamines AMINO SUGARS created by adding an amine group to a hexose sugar. Hexosamine
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D020650 Combinatorial Chemistry Techniques A technology, in which sets of reactions for solution or solid-phase synthesis, is used to create molecular libraries for analysis of compounds on a large scale. Chemistry Techniques, Combinatorial,Techniques, Combinatorial Chemistry,Chemistry Technic, Combinatorial,Chemistry Technics, Combinatorial,Chemistry Technique, Combinatorial,Combinatorial Chemistry Technic,Combinatorial Chemistry Technics,Combinatorial Chemistry Technique,Technic, Combinatorial Chemistry,Technics, Combinatorial Chemistry,Technique, Combinatorial Chemistry

Related Publications

Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-epsilon-iso-rhodomycinone.
December 2000, Carbohydrate research,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
New stereodivergent approach to 3-amino-2,3,6-trideoxysugars. Enantioselective synthesis of daunosamine, ristosamine, acosamine, and epi-daunosamine.
August 2003, Organic letters,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
Synthesis of L-daunosamine and L-ristosamine glycosides via photoinduced aziridination. Conversion to thioglycosides for use in glycosylation reactions.
October 2006, The Journal of organic chemistry,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
Synthesis of (S)-2-fluoro-L-daunosamine and (S)-2-fluoro-D-ristosamine.
July 1985, Carbohydrate research,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step.
January 2018, Beilstein journal of organic chemistry,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
Stereocontrolled routes to cis-hydroxyamino sugars, Part VII: Synthesis of daunosamine and ristosamine.
August 1986, Carbohydrate research,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
Regioselectivity of rhodium nitrene insertion. Syntheses of protected glycals of l-daunosamine, d-saccharosamine, and l-ristosamine.
April 2005, Organic letters,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
Synthesis of 3-amino-2,3,6-trideoxy-2-fluoro-L-talose and -D-allose [(R)-2-fluoro-L-daunosamine and (R)-2-fluoro-D-ristosamine].
January 1990, Carbohydrate research,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine.
November 1993, The Journal of antibiotics,
Feiqing Ding, and Ronny William, and Fei Wang, and Jimei Ma, and Li Ji, and Xue-Wei Liu
A stereoselective synthesis of 6,6,6-trifluoro-L-daunosamine and 6,6,6-trifluoro-L-acosamine.
July 2006, Organic & biomolecular chemistry,
Copied contents to your clipboard!