acosamine and ristosamine

acosamine has been researched along with ristosamine* in 4 studies

Other Studies

4 other study(ies) available for acosamine and ristosamine

ArticleYear
General Method for the Synthesis of α- or β-Deoxyaminoglycosides Bearing Basic Nitrogen.
    Journal of the American Chemical Society, 2021, 02-24, Volume: 143, Issue:7

    The introduction of glycosides bearing basic nitrogen is challenging using conventional Lewis acid-promoted pathways owing to competitive coordination of the amine to the Lewis acid promoter. Additionally, because many aminoglycosides lack a C2 substituent, diastereomeric mixtures of

    Topics: Glycosides; Hexosamines; Nitrogen; Peroxides; Stereoisomerism

2021
New stereodivergent approach to 3-amino-2,3,6-trideoxysugars. Enantioselective synthesis of daunosamine, ristosamine, acosamine, and epi-daunosamine.
    Organic letters, 2003, Aug-21, Volume: 5, Issue:17

    [reaction: see text] An enantioselective preparation of the four diastereomeric 3-amino-2,3,6-trideoxy-hexoses, key components of anthracycline antibiotics, has been developed. Sharpless catalytic asymmetric epoxidation of the (2E)-2,5-hexadien-1-ol, regioselective ring opening with azide, followed by convenient functional group transformations, afforded the key aldehydes cis- or trans-6 in any configuration. The diastereoselective addition of methylmetal reagents to these aldehydes followed by ozonolysis gives access in a completely stereocontrolled manner to the four isomeric trideoxyaminosugars.

    Topics: Aldehydes; Azides; Carbohydrate Conformation; Hexosamines; Methylation; Ozone; Stereoisomerism

2003
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.
    Carbohydrate research, 2000, Dec-01, Volume: 329, Issue:4

    3-Amino-2,3,6-trideoxyhexopyranoses are essential constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-epsilon-isorhodomycinone.

    Topics: Anthracyclines; Antibiotics, Antineoplastic; Doxorubicin; Drug Screening Assays, Antitumor; Hexosamines; Humans; Molecular Structure; Rhamnose; Stereoisomerism; Tumor Cells, Cultured

2000
Synthesis and evaluation of antiviral activity of L-acosamine and L-ristosamine nucleosides of furanose configuration.
    Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 1991, Volume: 45, Issue:6

    Mercuric-catalyzed hydrolysis of acetylated L-rhamnal 1 gives an alpha,beta-unsaturated aldehyde 2. 1,4-Addition of DBU-phthalimide salt with concomitant acetyl shift resulted in L-ribo and L-arabino isomers of 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-hexofuranose 3 and 4. After acetylation at the anomeric center, coupling with silylated thymine resulted in three new nucleosides, with L-acosamine and L-ristosamine of furanose configuration as the carbohydrate moiety. The target compounds have been evaluated for their antiviral activity against HIV and HSV-1.

    Topics: Antiviral Agents; Carbohydrate Conformation; Cell Line; Hexosamines; HIV-1; Humans; Indicators and Reagents; Isomerism; Molecular Structure; Nucleosides; Simplexvirus

1991