BIOMAT Database Logo BIOMAT Database Logo

Stereoselective synthesis of (+)-1-deoxyaltronojirimycin. 2016

Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
a Department of Chemistry, CNR-IBPM , Sapienza University of Rome , Rome , Italy.

A stereocontrolled, facile and high-yield approach for producing (+)-altroDNJ, has been developed starting from the inexpensive commercial cis 2-butene-1,4-diol. Sharpless epoxidation and a subsequent dihydroxylation were used for the introduction of all stereocentres; finally, the ring closure under basic conditions afforded the piperidine heterocycle.

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
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D004852 Epoxy Compounds Organic compounds that include a cyclic ether with three ring atoms in their structure. They are commonly used as precursors for POLYMERS such as EPOXY RESINS. Epoxide,Epoxides,Epoxy Compound,Oxiranes,Compound, Epoxy,Compounds, Epoxy
D006571 Heterocyclic Compounds Cyclic compounds that include atoms other than carbon in their ring structure. Heterocyclic Compound,Compound, Heterocyclic,Compounds, Heterocyclic
D006900 Hydroxylation Placing of a hydroxyl group on a compound in a position where one did not exist before. (Stedman, 26th ed) Hydroxylations
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
D017485 1-Deoxynojirimycin An alpha-glucosidase inhibitor with antiviral action. Derivatives of deoxynojirimycin may have anti-HIV activity. 1,5-Deoxy-1,5-imino-D-mannitol,1-Deoxymannojirimycin,1,5-Dideoxy-1,5-imino-D-mannitol,1-Deoxynojirimycin Hydrochloride,Bay n 5595,Moranoline,1 Deoxymannojirimycin,1 Deoxynojirimycin,1 Deoxynojirimycin Hydrochloride

Related Publications

Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Rapid and practical synthesis of (-)-1-deoxyaltronojirimycin.
February 2011, Organic & biomolecular chemistry,
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
An oxidation and ring contraction approach to the synthesis of (+/-)-1-deoxynojirimycin and (+/-)-1-deoxyaltronojirimycin.
January 2010, Organic letters,
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Stereoselective Synthesis of Tilivalline(1).
October 1998, The Journal of organic chemistry,
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Stereoselective synthesis of 1'-functionalized-4'-thionucleosides.
January 2007, Nucleosides, nucleotides & nucleic acids,
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Diastereoselective Synthesis of 1-Deoxygalactonojirimycin, 1-Deoxyaltronojirimycin, and N-Boc-(2S,3S)-3-Hydroxypipecolic Acid via Proline Catalyzed α-Aminoxylation of Aldehydes.
May 2015, The Journal of organic chemistry,
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Stereoselective synthesis of highly substituted 1-isomorphans (1-azabicyclo[3.3.1]nonanes).
July 2023, Chemical communications (Cambridge, England),
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Titanium(IV)-catalyzed stereoselective synthesis of spirooxindole-1-pyrrolines.
December 2014, Organic letters,
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Stereoselective Synthesis of HIV-1 Protease Inhibitor, DMP 323.
January 1996, The Journal of organic chemistry,
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-l-serinal.
November 2016, The Journal of organic chemistry,
Giuliana Righi, and Emanuela Mandic', and Ilaria Tirotta, and Gaia Clara Mercedes Naponiello, and Carla Sappino, and Cristina Marucci, and Michela Tomei, and Paolo Bovicelli
Stereoselective Approach for the Synthesis of Diverse 1'-Modified Carbanucleosides.
November 2023, Organic letters,
Copied contents to your clipboard!