4,5-anhydro-1,2,3-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-L-threo-pent-1-enitol | 666726-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4,5-anhydro-1,2,3-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-L-threo-pent-1-enitol
• 英文别名: 2-[(1S)-1-(2R)-oxiranyl-2-propenyl]-1H-isoindole-1,3(2H)-dione；2-((s)-1-((r)-Oxiran-2-yl)allyl)isoindoline-1,3-dione；2-[(1S)-1-[(2R)-oxiran-2-yl]prop-2-enyl]isoindole-1,3-dione
• CAS: 666726-10-9
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: FSLGJLSRUPPDPH-QWRGUYRKSA-N

物化性质

• 沸点：
  363.9±25.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-anhydro-1,2,3-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-L-threo-pent-1-enitol 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 (叔丁基亚氨基)三(吡咯烷)膦 、 肼 作用下， 以 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 7.0h， 生成 1,3,4,5-tetradeoxy-3-{[(2-{[(1-methylethyl)oxy]carbonyl}phenyl)carbonyl]amino}-1-[[(1R)-1-methyl-2-propen-1-yl](2-pyridinylsulfonyl)amino]-L-threo-pent-4-enitol
  参考文献：
  名称：

  Development of a Robust Ring-Closing Metathesis Reaction in the Synthesis of SB-462795, a Cathepsin K Inhibitor

  摘要：

  The development of a robust and high-yielding ring-closing metathesis (RCM) reaction and its demonstration on multikilogram scale are described. A detailed understanding of the impact of impurities on the RCM reaction was achieved using a variety of chemical and statistical methods. Specifically, individual impurities were evaluated in spiking studies to identify those that negatively affected the RCM reaction. Projection methods (PCA and PLS) were applied to historical data to identify the main sources of variation in starting material quality and determine the main detrimental impurities that impeded the RCM reaction. The synthesis of the starting material was then modified to adequately control these key impurities, which in turn ensured a robust RCM process. Finally, the robustness of the RCM reaction was assessed using a probability-based approach.

  DOI：

  10.1021/op700288p
• 作为产物：
  描述：

  1,2,3-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-O-[(4-methylphenyl)sulfonyl]-L-threo-pent-1-enitol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 4,5-anhydro-1,2,3-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-L-threo-pent-1-enitol
  参考文献：
  名称：

  Large-scale synthesis of SB-462795, a cathepsin K inhibitor: the RCM-based approaches

  摘要：

  Two stereoselective syntheses of SB-462795, a highly potent cathepsin K inhibitor, are described. Both routes feature a C5-C6 disconnection by ring closing metathesis to construct an azepane ring and are amenable to large-scale manufacturing. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.022

文献信息

• Method of Preparation of Benzofuran-2-Carboxylic Acid -Amide
  申请人：Clark William M.

  公开号：US20080262224A1

  公开（公告）日：2008-10-23

  This invention relates to a method of preparation of benzofuran-2-carboxylic acid (S)-3-methyl- 1 -[(4S,7R)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide.

  这项发明涉及一种制备苯并呋喃-2-羧酸(S)-3-甲基-1-[(4S,7R)-7-甲基-3-氧代-1-(吡啶-2-磺酰基)-氮杂庚-4-基甲酰]-丁基}-酰胺的方法。
• [EN] RECOVERY OF OPTICALLY ACTIVE EPOXY ALCOHOLS<br/>[FR] RECUPERATION D'EPOXY ALCOOLS OPTIQUEMENT ACTIFS
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005123708A1

  公开（公告）日：2005-12-29

  A process to recover optically active epoxy alcohols from asymmetric epoxidation reaction mixtures such as those produced using the Sharpless method of epoxidation of allylic alcohols. The process includes adding a reducing agent to reduce an organic hydroperoxide in the asymmetric epoxidation reaction product to a corresponding alcohol to form a reduced epoxidation reaction mixture; adding the reduced reaction product to a film evaporation unit to form a residue fraction and an optically active epoxy alcohol distillate fraction; and distilling the optically active epoxy alcohol distillate fraction to purify the optically active epoxy alcohol.

  从不对称环氧化反应混合物中回收光学活性环氧醇的过程，例如使用Sharpless方法环氧化烯丙醇所产生的混合物。该过程包括添加还原剂以将不对称环氧化反应产物中的有机过氧化物还原为相应的醇，形成还原环氧化反应混合物；将还原反应产物添加到薄膜蒸发装置中，形成残留物分数和光学活性环氧醇馏分；并蒸馏光学活性环氧醇馏分以纯化光学活性环氧醇。
• Protease inhibitors
  申请人：Bondinell E William

  公开号：US20060052365A1

  公开（公告）日：2006-03-09

  This invention relates 4-amino-azepan-3-ones of formula (I) which are useful as protease inhibitors, particularly of cathepsin S, and as such are useful for preventing a number of diseases amongst which are atherosclerotic lesions and pulmonary diseases such as asthma and allergic reactions.

  这项发明涉及式（I）的4-氨基-氮杂七环-3-酮，它们可用作蛋白酶抑制剂，特别是卡特普辛S的抑制剂，并且作为预防多种疾病的有用药物，其中包括动脉粥样硬化病变和肺部疾病，如哮喘和过敏反应。
• PROTEASE INHIBITORS
  申请人：SmithKline Beecham Corporation

  公开号：EP1539178A2

  公开（公告）日：2005-06-15
• METHOD OF PREPARATION OF BENZOFURAN-2-CARBOXYLIC ACID (S)-3-METHYL-1- ((4S, 7R)-7METHYL-3-OXO-1-(PYRIDINE-2-SULFONYL)-AZ EPAN-4-YLCARBAMOYL-BUTYL)-AMIDE
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1713790A2

  公开（公告）日：2006-10-25