首页> 外国专利> A NOVEL PROCESS FOR THE FOUR STEP PROTECTING GROUP FREE SYNTHESIS OF (+)-HAGEN'S GLAND LACTONES

A NOVEL PROCESS FOR THE FOUR STEP PROTECTING GROUP FREE SYNTHESIS OF (+)-HAGEN'S GLAND LACTONES

机译:四步保护(+)-哈根腺内酯的四步自由合成的新方法

摘要

This invention relates to a process for preparing (+)-Hagen"s gland lactones of formula (1) comprising the following steps (a)Treating D-glucono- 5-lactone formula (2) with hydrogen bromide in acetic acid followed by Zn powder in 50% acetic acid in water at ambient temperature to obtain (3R,4R)-3,4-dihydroxy-5-hexenoic acid-y-lactone formula(3). Olefin cross metathesis reaction between hydroxyl lactone(3) obtained in step (a) and an alkene using Grubbs second-generation catalyst in anhydrous CH2CI2 under conditions effective to yield a compound of formula (4a/4b). (c) Iodine-mediated cyclization reaction of olefin compound (4a/4b) in dry acetonitrile by using iodine and NaHC03 under conditions effective to yield iodolactones (5a/5b) and its diastereomers (6a/6b). (d) Reductive removal of iodine from iodolactone (5a/5b) using nBu3SnH and AIBN in benzene under refluxing conditions to provide Hagen"s gland lactones (la/lb).
机译:本发明涉及一种制备式(1)的(+)-哈根腺内酯的方法,该方法包括以下步骤(a)在乙酸中先用溴化氢再用Zn处理D-葡萄糖基-5-内酯式(2)。在室温下于50%的乙酸水溶液中制成粉末,制得(3R,4R)-3,4-二羟基-5-己酸-γ-内酯式(3)。羟基内酯之间的烯烃交叉复分解反应(3)步骤(a)和在无水CH 2 Cl 2中使用Grubbs第二代催化剂的烯烃,在有效产生式(4a / 4b)化合物的条件下;(c)碘介导的烯烃化合物(4a / 4b)在无水乙腈中的环化反应通过在有效产生碘内酯(5a / 5b)及其非对映异构体(6a / 6b)的条件下使用碘和NaHCO3(d)在回流条件下,使用nBu3SnH和AIBN在苯中使用碘化钠还原从碘内酯(5a / 5b)中去除碘哈根氏腺内酯(la / lb)。

著录项

  • 公开/公告号IN2012MU01908A

    专利类型

  • 公开/公告日2014-01-10

    原文格式PDF

  • 申请/专利权人

    申请/专利号IN1908/MUM/2012

  • 发明设计人 K PULLAIAH;PRO RODNEY A FERNANDES;

    申请日2012-07-02

  • 分类号C07D309/30;A61K31/351;

  • 国家 IN

  • 入库时间 2022-08-21 15:57:36

相似文献

  • 专利
  • 外文文献
  • 中文文献
获取专利

客服邮箱:kefu@zhangqiaokeyan.com

京公网安备:11010802029741号 ICP备案号:京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有
  • 客服微信

  • 服务号