(E)-17-(isocyanotosylmethylene)-3-methoxyandrosta-3,5,9(11)-triene | 93206-68-9

• 英文名称: (E)-17-(isocyanotosylmethylene)-3-methoxyandrosta-3,5,9(11)-triene
• CAS: 93206-68-9
• 化学式: C₂₉H₃₃NO₃S
• 分子量: 475.652
• InChiKey: LDFVADADUCIKIF-WMYJXWSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  (E)-17-(isocyanotosylmethylene)-3-methoxyandrosta-3,5,9(11)-triene 在 苄基三乙基氯化铵 sodium hydroxide 、 硫酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 23.0h， 生成 21-Hydroxypregna-4,9(11),16-triene-3,20-dione
  参考文献：
  名称：

  Synthesis of 17-(2-Methoxy-3-oxazolin-4-yl)-, 17-(3-Oxazolin-4-yl)-, and 17-(2-Oxazolin-4-ylidene) Substituted Steroids and Their Use as Precursors of Corticosteroids

  摘要：

  17-(Isocyanotosylmethylene)steroids 4 are useful intermediates in the conversion of 17-oxosteroids into 17-(hydroxyacetyl)steroids. The 21-CH2OH group is effectively introduced by a base-mediated reaction of compounds 4 with formaldehyde and MeOH to give 17-(2-methoxy-3-oxazolin-4-yl) derivatives 12, which by acid hydrolysis give 17-(hydroxyacetyl)steroids 10 and 16 in high yields. Partial hydrolysis of the same oxazoline derivatives 12 provides the 17-(hydroxyacetyl) cortico side chain of 13 equipped with a formyl-protected hydroxy group. 3-Oxazolinyl and 2-oxazolinylidene steroid derivatives 19, 20, and 21, without a 2-methoxy substituent, are discussed as alternatives of 12.

  DOI：

  10.1021/jo00098a024
• 作为产物：
  描述：

  在 二异丙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到(E)-17-(isocyanotosylmethylene)-3-methoxyandrosta-3,5,9(11)-triene
  参考文献：
  名称：

  Leusen, Daan van; Leusen, Albert M. van, Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 10, p. 393 - 401

  摘要：

  DOI：

文献信息

• Synthesis of 20-oxo steroids
  作者：Daan van Leusen、Erik van Echten、Albert M. van Leusen

  DOI：10.1002/recl.19921111102

  日期：——

  The synthesis is described of a series of eighteen 16-dehydro-20-isocyano-20-sulfonylpregnanes (5 and 8–14) by C-20 alkylation of 17-[isocyano(sulfonyl)methylene]androstanes 1–3. The geminal isocyano and sulfonyl groups at C-20 (compounds 5, 8–14) are removed by acid hydrolysis to provide a new entry into 20-oxo steroids (6, 15–19). The C-20 alkylation also includes halomethylation and alkoxymethylation

  通过17- [异氰基（磺酰基）亚甲基] Androstanes 1-3的C-20烷基化反应，描述了18个16-脱氢-20-异氰基20-磺酰基孕烯的合成（5和8-14）。通过酸水解将C-20上的双异氰酸酯基和磺酰基基团（化合物5、8–14）除去，以提供新的进入20-氧代类固醇的能力（6、15–19）。C-20烷基化还包括卤甲基化和烷氧基甲基化，以分别形成21-卤-和21-烷氧基-16-脱氢-20-氧杂戊烷。作为酸水解的一种有吸引力的替代方法，首先用Pb（OAc）4氧化异氰基水解成异氰酸酯基之前（双异氰酸酯基和磺酰基基团）水解成相同的20-氧代甾族化合物 后一种转化是在室温下在非酸性条件下在氧化铝在二氯甲烷中的浆液中进行的。
• New process for the preparation of 21-hydroxy-20-keto-delta 16-steroids and new intermediate compounds formed in this process
  申请人：GIST-BROCADES N.V.

  公开号：EP0123736A1

  公开（公告）日：1984-11-07

  The invention relates to a new process for the preparation of 21-hydroxy-20-keto-steroids from 17-isocyano-sulfonylmethylene-steroids whereby simultaneously an unsaturated bond is introduced between C16 and C17. Furthermore, the invention relates to new intermediate compounds formed in this process and their preparation.

  本发明涉及一种从 17-异氰基磺酰亚甲基类固醇制备 21-羟基-20-酮类固醇的新工艺，在该工艺中，同时在 C16 和 C17 之间引入不饱和键。此外，本发明还涉及在该工艺中形成的新中间化合物及其制备方法。
• A novel method to build acetyl and hydroxyacetyl side-chains in 17-oxosteroids
  作者：Daan van Leusen、Albert M. van Leusen

  DOI：10.1016/s0040-4039(01)81236-3

  日期：1984.1
• 17-(Isocyano-sulfonylmethylene)-steroids, 17-(formamido-sulfonylmethylene)-steroids and their preparation
  申请人：GIST-BROCADES N.V.

  公开号：EP0124934B1

  公开（公告）日：1986-11-20
• New process for the preparation of 20-keto-delta16-steroids and new intermediate compounds formed in this process
  申请人：GIST-BROCADES N.V.

  公开号：EP0127217B1

  公开（公告）日：1988-11-02