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    Process for making lincomycin and analogs thereof and novel compounds obtained thereby
    27.
    发明授权
    Process for making lincomycin and analogs thereof and novel compounds obtained thereby 失效
    制备LINCOMYCIN及其类似物及其获得的新化合物的方法

    公开(公告)号：US3692767A

    公开(公告)日：1972-09-19

    申请号：US3692767D

    申请日：1970-05-06

    Applicant: UPJOHN CO

    Inventor： MAGERLEIN BARNEY J

    IPC: B01F15/04 ,  C07H15/16 ,  C07C47/18

    CPC classification number: C07H15/16 ,  B01F15/04

    Abstract: Lincomycin is formed by tosylating methyl 1-thio- Alpha -Dgalacto-octopyranoside to form methyl 6-O-(p-toluenesulfonyl)-1thio- Alpha -D-galactopyranoside, acylating the resulting compound to form the peracylate, replacing the tosyl group with iodine to form peracylated methyl 6-deoxy-6-iodo-1-thio- Alpha D-galactopyranoside, replacing the iodo group by a nitro group to form peracylated methyl 6-deoxy-6-nitro-1-thio- Alpha -Dgalactopyranoside, treating the latter with acetaldehyde and sodium methoxide to form methyl 6-deamino-6-nitro- Alpha thiolincosaminide, reducing the latter with lithium aluminum hydride to form methyl Alpha -thiolincosaminide, and acylating the latter with trans-1-methyl-4-propyl-L-2-pyrrolidinecarboxylic acid. By substituting other aldehydes and/or other 1-thio- Alpha -D-galactopyranosides, analogs of lincomycin are obtained.

    Abstract translation: 通过将1-硫代-α-D-半乳糖 - 辛吡喃甲酸甲苯磺酰化形成甲基纤维素形成6-O-（对甲苯磺酰基）-1-硫代-α-D-吡喃半乳糖苷甲基酯，酰化所得化合物以形成过苯甲酸酯，代替 甲苯磺酰基与碘形成过酰基化甲基6-脱氧-6-碘-1-硫代-α-D-吡喃半乳糖苷，用碘基代替碘代，形成过酰基化甲基6-脱氧-6-硝基-1-硫代 - α-D-吡喃半乳糖苷，用乙醛和甲醇钠处理后者，形成6-脱氨基-6-硝基-α-硫代吗啉氨基甲酸酯，用氢化铝锂还原后者，形成α-硫代氨基甲酰甲酰甲酯，并用反式 -1-甲基-4-丙基-L-2-吡咯烷羧酸。 通过用其他醛和/或其它1-硫代-α-D-吡喃半乳糖苷取代，可以得到林可霉素的类似物。

    7-mercapto-7-deoxylincomycins and process for preparing the same
    28.
    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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