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    Process for making 7-chloro-7-deoxylincomycin and related compounds and novel intermediates produced therein
    3.
    发明授权
    Process for making 7-chloro-7-deoxylincomycin and related compounds and novel intermediates produced therein 失效
    制备7-氯-7-去氧吗啉的方法及相关化合物及其生产的新型中间体

    公开(公告)号：US3574186A

    公开(公告)日：1971-04-06

    申请号：US3574186D

    申请日：1969-10-08

    Applicant: UPJOHN CO

    Inventor： BIRKENMEYER ROBERT D ,  KAGAN FRED

    IPC: C07D207/22 ,  C07H15/16 ,  C07C47/18

    CPC classification number: C07D207/22 ,  C07H15/16 ,  Y10S516/07

    Abstract: COMPOUNDS OF THE FORMULA:

    2-(R-S-),3,4,5-TRI(HO-),6-(CH3-CH(-CL)-CH(-NH-AC)-)-

    TETRAHYDROPYRAN

    ARE PREPARED BY REPLACING BY CHLORINE, THE 7-HYDROXY OF A COMPOUND OF THE FORMULA:

    2-(R-S-),3,4,5-TRI(HO-),6-(CH3-CH(-OH)-CH(-NH-AC)-)-

    TETRAHYDROPYRAN

    THE REPLACEMENT IS EFFECTED BY (1) MIXING THE STARTING COMPOUND OF FORMULA II WITH THIONYL CHLORIDE, (2) HEATING WITH THIONYL CHLORIDE, AND (3) HYDROLYSIS. THIONYL CHLORIDE WITHOUT HEATING CONVERTS THE COMPOUNDS OF FORMULA II TO A 3,4-O-CYCLIC SULFITE OF THE FORMULA:

    HEATING WITH THIONYL CHLORIDE CONVERTS COMPOUNDS OF FORMULAS II AND III TO A 3,4-O-CYCLIC SULFITE OF THE FORMULA:

    PERHYDRO-1,3,2-DIOXATHIOLO(4,5-C)PYRAN

    2-(O=),4-(CH3-CH(-OH)-CH(-NH-AC)-),6-(R-S-),7-(HO-)-
    SOLVOLYSIS CONVERTS COMPOUNDS OF FORMULAS IV AND V TO A 7-CHLORO-7DEOXYLINCOMYCIN OF FORMULA I.

    PERHYDRO-1,3,2-DIOXATHIOLO(4,5-C)PYRAN

    (2-(O=),4-(CH3-CH(-CL)-CH(-NH-AC)-),6-(R-S-),7-(HO-)-

    AND A BIS-SULFITE OF THE FORMULA:

    PERHYDRO-1,3,2-DIOXATHIOLO(4,5-C)PYRAN

    2-(O=),4-(CH3-CH(-CL)-CH(-NH-AC)-),6-(R-S-),7-(HO-)-

    7-mercapto-7-deoxylincomycins and process for preparing the same
    7.
    发明授权
    7-mercapto-7-deoxylincomycins and process for preparing the same 失效
    7-MERCAPTO-7-去氧肾上腺素及其制备方法

    公开(公告)号：US3689474A

    公开(公告)日：1972-09-05

    申请号：US3689474D

    申请日：1970-08-04

    Applicant: UPJOHN CO

    Inventor： KAGAN FRED ,  MAGERLEIN BARNEY J

    IPC: C07H15/16 ,  C07G11/00

    CPC classification number: C07H15/16

    Abstract: WHICH ON ACYLATION YIELDS COMPOUNDS OF FORMULA I.

    HYDROPYRAN

    2-(R-S-),3,4,5-TRI(HO-),6-(CH3-CH(-SH)-CH(-NH2)-)TETRA-

    AND HEATING IT WITH HYDROGEN SULFIDE IN AN INERT SOLVENT FOR FORM A COMPOUND OF THE FORMULA:

    PYRAN

    2-(R-S-),3,4,5-TRI(HO-),6-((-CH(-CH3)-NH-)>CH-)TETRAHYDRO-

    AN INERT SOLVENT IN THE PRESENCE OF AN ACID ACCEPTOR, THE 2-, 3-, AND 4-HYDROXY GROUP MAY BE COVERSED WITH PROTECTIVE GROUPS, TO FORM A NOVEL COMPOUND OF THE FORMULA:

    HYDROPYRAN

    2-(R-S-),3,4,5-TRI(HO-),6-(CH3-CH(-HALO)-CH(-NH2)-)TETRA-

    ARE PREPARED BY HEATING A COMPOUND OF THE FORMULA:

    TETRAHYDROPYRAN

    2-(R-S-),3,4,5-TRI(HO-),6-(CH3-CH(-SH)-CH(-NH-CO-R4)-)

    ANTIBACTERIAL COMPOUNDS OF THE FORMULA:

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