logo
    ChemInform Abstract: A Dramatic Concentration Effect on the Stereoselectivity of N‐Glycosylation for the Synthesis of 2′‐Deoxy‐β‐ribonucleosides.
    ChemInform (2012)
    Fei YangYugen ZhuBiao Yu
    0
    Citation
    1
    Reference
    10
    Related Paper
    Abstract:
    Abstract The stereoselectivity of the N‐glycosylation reaction of purines and uracils with hexynylbenzoate (I) depends on the concentration of the reaction solution leading to higher β/α‐ratio at lower concentrations.
    Topics:
    Biochemical and Molecular Research
    HIV/AIDS drug development and treatment
    DNA and Nucleic Acid Chemistry
    ChemInform Abstract: Stereoselective Reactions. Part 13. Total Synthesis of (+)‐Sesbanine by a Highly Stereoselective Cycloanellation Reaction.
    ChemInform (1988)
    Kiyoshi TomiokaKenji Koga
    Abstract The cycloanellation reaction is first studied for some model compounds and thereupon used as starting step in the synthesis of the title compound (VII).
    Citations (0)
    Semiempirical calculations on the mechanism of stereoselective NaBH4 reduction of 2-methoxycarbonyl-2-allyl-cyclopentanone
    Journal of Molecular Structure THEOCHEM (1995)
    Carlos Maurício R. Sant’AnnaRicardo Bicca de AlencastroEliezer J. BarreiroCarlos Alberto Manssour Fraga
    Cyclopentanone
    Citations (3)
    Pentafulvene-derived η3-allyltitanocenes as intermediates for the stereoselective functionalization of 5-membered carbocycles
    Chemical Communications (2013)
    Jomy K. JosephFlorian JaroschikK. V. RadhakrishnanJean‐Luc VasseJan Szymoniak
    Allyltitanocene complexes can be generated by reacting pentafulvenes with DIBAL-H and Cp2TiCl2. Their coupling with aldehydes affords homoallylic alcohols in a highly regio- and stereoselective manner. The potential of this method for the stereoselective synthesis of cyclopentane derivatives is illustrated.
    Cyclopentanes
    Surface Modification
    Citations (9)
    Regio- and stereoselective synthesis of polysubstituted 5-hydroxypyrrolidin-2-ones from 3-alkoxysuccinimides
    Tetrahedron Letters (2019)
    Fábio Moreira da SilvaAndreia M. P. W. da SilvaMateus MittersteinerValquiria P. AndradeEstefania da C. Aquino
    Moiety
    Succinimides
    Citations (5)
    The Stereoselective Hydrogenation of Nepetalactoles. The Role of C1 Alkoxyl Groups on the Stereoselectivity
    Heterocycles (1993)
    Takeshi WakamatsuMasaharu KigawaMasahide TanakaTakao KatsuharaKoh Sugama
    Citations (3)
    Catalyst-Controlled Stereoselective Construction of Indole-Fused Heterocycles through Cycloadditions of Indolyl-Allenes: A Theoretical Investigation
    Russian Journal of Physical Chemistry A (2021)
    Hongliang Ren
    Tandem
    Citations (0)
    Stereoselective synthesis of (±)-ancistrofuran: stereoselective reduction of a γ-hydroxyketone
    Journal of the Chemical Society Chemical Communications (1984)
    Raymond BakerPaul RavenscroftChristopher J. Swain
    A remarkably stereoselective reduction of a γ-hydroxyketone with two equiv. of lithium triethylborohydride has been observed and this effect has been suggested to originate from 'chelation control'; the reaction has been utilised in a short stereoselective synthesis of ancistrofuran.
    Citations (14)
    Stereoselective α-Glycosylation with 3-O-Acetylated d-Gluco Donors
    Synlett (2006)
    Nikolay E. NifantievNadezhda E. UstyuzhaninaBozhena S. KomarovaNatalya S. ZlotinaVadim B. Krylov
    The effect of a 3-O-acetyl group on the stereoselectivity of α-glycosylation with 2-O-benzylated d-gluco glycosyl donors was studied. It was shown that 3-O-acetylated donors gave α-anomers predominantly or exclusively, whereas glycosylation with the corresponding per-O-benzylated donors afforded mixtures of comparable amounts of α- and β-anomers. The higher α-stereoselectivity in the first case was accounted for by the remote anchimeric assistance of the 3-O-acetyl group, which was confirmed by theoretical calculations.
    Glycosyl donor
    Chemoselectivity
    Citations (23)
    Stereoselective reduction of α-hydroxy ketones
    Tetrahedron Letters (1983)
    Tadashi NakataTadasu TanakaTakeshi Oishi
    ALUMINUM HYDRIDE
    Diastereomer
    Citations (145)
    Trityl Salt Catalyzed Stereoselective Glycosylation of Alcohols with 1-Hydroxyribofuranose
    Chemistry Letters (1996)
    Hiromi UchiroTeruaki Mukaiyama
    Abstract In the presence of a catalytic amount of several trityl salts, 2,3,5-tri-O-benzyl-d-ribofuranose smoothly reacted with alcohols to give various β-ribofuranosides in high yields with high stereoselectivity while reversed stereoselectivity was observed in the coexistence of lithium perchlolate.
    Citations (35)