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    • 1. 发明申请
    • Stereospecific reduction of Sapogen-3-ones
    • 皂苷-3-酮的立体特异性还原
    • US20060041119A1
    • 2006-02-23
    • US10531086
    • 2003-04-28
    • Philip GunningPeter Tiffin
    • Philip GunningPeter Tiffin
    • C07J71/00
    • C07J71/0005
    • A method to stereospecifically prepare a steroidal sapogenin or a derivative thereof by reducing a 3-keto,5β-H steroidal sapogenin with a hindered organoborane or an organo-aluminium hydride. A 3β-hydroxy,5β-H steroidal sapogenin or derivative thereof may be prepared by reducing the 3-keto,5β-H steroidal sapogenin using as reducing agent a relatively highly hindered organoborane reagent or by SN 2 inversion of a 3α-hydroxy,5β-H steroidal sapogenin or derivative thereof. The organo-aluminium hydride may be used to prepare a 3α,5β-H steroidal sapogenin or derivative thereof. The invention provides a convenient route to useful steroidal sapogenins such as sarsasapogenin, episarsasapogenin, smilagenin, epismilagenin and esters thereof, from readily available or easily preparable starting materials (e.g. diosgenone, preparable from diosgenin).
    • 通过用受阻的有机硼烷或有机氢化铝还原3-酮基,5β-H甾体皂苷元,立体选择性地制备甾体皂苷元或其衍生物的方法。 可以通过使用相对高度受阻的有机硼烷试剂的还原剂或通过3α-羟基,5β的SN 2反转来还原3-酮基,5β-H甾体皂苷元来制备3β-羟基,5β-H甾体皂苷元或其衍生物 -H甾体皂苷元或其衍生物。 有机铝氢化物可用于制备3α,5β-H甾体皂苷元或其衍生物。 本发明提供了从易得的或易于制备的起始物质(例如,由薯os皂苷配制的脱水梭子),可用于甾体皂苷元的方便途径,例如萨洒皂草配基,季节调节素,镰刀菌素,epismilagenin及其酯。