BIOMAT Database Logo BIOMAT Database Logo

Stereocontrolled routes to cis-hydroxyamino sugars, Part VII: Synthesis of daunosamine and ristosamine. 1986

H W Pauls, and B Fraser-Reid

The nitrogen of an allylic amine can serve as the fulcrum for stereocontrolled delivery of oxygen to an adjacent trigonal site, and cis-hydroxyamino sugars can thus be prepared. Methods for achieving the complementary procedure, namely, control of the delivery of nitrogen to an adjacent site by an allylic oxygen, are described. For example, treatment of methyl 2,3,6-trideoxy-alpha-L-erythro-hex-2-enopyranoside with trichloroacetonitrile gave an imidate ester which reacted with iodonium dicollidine perchlorate to give 2-trichloromethyl-(methyl 2,3,4,6-tetradeoxy-2-iodo-alpha-L-altropyranosido)-[3,4-d]-2-oxazo line. Exhaustive reductive dehalogenation of this product followed by hydrolysis led to methyl N-acetyl-alpha-L-ristosaminide. An analogous series of reactions was used to prepare the corresponding daunosaminide.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009904 Optical Rotation The rotation of linearly polarized light as it passes through various media. Optical Activity,Activity, Optical,Rotation, Optical
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
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

Related Publications

H W Pauls, and B Fraser-Reid
New stereodivergent approach to 3-amino-2,3,6-trideoxysugars. Enantioselective synthesis of daunosamine, ristosamine, acosamine, and epi-daunosamine.
August 2003, Organic letters,
H W Pauls, and B Fraser-Reid
Synthesis of (S)-2-fluoro-L-daunosamine and (S)-2-fluoro-D-ristosamine.
July 1985, Carbohydrate research,
H W Pauls, and B Fraser-Reid
A short and highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides.
February 2011, Organic letters,
H W Pauls, and B Fraser-Reid
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,
H W Pauls, and B Fraser-Reid
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,
H W Pauls, and B Fraser-Reid
Engineering enzymes for chemoenzymatic synthesis. Part I: Practical routes to aza-sugars and complex carbohydrates.
October 1992, Trends in biotechnology,
H W Pauls, and B Fraser-Reid
A pericyclic cascade to the stereocontrolled synthesis of 9-cis-retinoids
May 2000, The Journal of organic chemistry,
H W Pauls, and B Fraser-Reid
Regioselectivity of rhodium nitrene insertion. Syntheses of protected glycals of l-daunosamine, d-saccharosamine, and l-ristosamine.
April 2005, Organic letters,
H W Pauls, and B Fraser-Reid
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,
H W Pauls, and B Fraser-Reid
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,
Copied contents to your clipboard!