A HIGHLY EFFICIENT GLYCOSYLATION CHEMISTRY ENABLED BY A DIRECTING GROUP THAT IS PART OF THE ANOMERIC LEAVING GROUP

    公开(公告)号:US20240132530A1

    公开(公告)日:2024-04-25

    申请号:US18262878

    申请日:2022-01-28

    IPC分类号: C07H1/00

    CPC分类号: C07H1/00

    摘要: Broadly applicable and stereoselective formation of glycosidic linkage remains challenging yet of critical importance in giycoscience. By developing an SN2 glycosylation, this work advances a general solution to this challenge via stereoinversion at the anomeric position of glycosyl ester donors. This SN2 process is enabled by a basic directing-group in the leaving-group, which is activated by a cationic gold catalyst or any other electrophilic reagent. Unlike all the reported directing group approaches, this strategy is applicable to any glycosyl donors—a long sought-after yet unmet goal in carbohydrate chemistry; moreover, the basic directing-group upon glycosylation is lost as part of the leaving-group and hence traceless in the glycoside products, therefore avoiding potential complications in downstream transformations. Highly selective construction of glycosidic bonds including challenging 1,2-cis glycosidic bonds is achieved in excellent yields. The strategy is applied iteratively to access oligosaccharides and can distinguish alcohols with different steric hindrance.

    METHODS OF PREPARING NICOTINAMIDE RIBOSIDE AND DERIVATIVES THEREOF

    公开(公告)号:US20240101588A1

    公开(公告)日:2024-03-28

    申请号:US18307733

    申请日:2023-04-26

    IPC分类号: C07H19/048 C07H1/00 C07H1/06

    摘要: Methods of preparing nicotinamide riboside and derivatives thereof. In an aspect, the invention relates to a method of preparing a compound of formula (I)




    wherein



    n is 0 or 1;
    m is 0 or 1;
    Y is O or S;
    R1 is selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted primary or secondary amino, and substituted or unsubstituted azido;
    R2-R5, which may be the same or different, are each independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, and substituted or unsubstituted aryl; and
    X− is an anion, selected from an anion of a substituted or unsubstituted carboxylic acid, a halide, a substituted or unsubstituted sulfonate, a substituted or unsubstituted phosphate, a substituted or unsubstituted sulfate, a substituted or unsubstituted carbonate, and a substituted or unsubstituted carbamate.