(S)-5-(2-Mesyloxyethyl)-2,2-dimethyl[1,3]dioxolan-4-one | 188908-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-(2-Mesyloxyethyl)-2,2-dimethyl[1,3]dioxolan-4-one
• 英文别名: 2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]ethyl methanesulfonate
• CAS: 188908-62-5
• 化学式: C₈H₁₄O₆S
• 分子量: 238.262
• InChiKey: BAKGJYVYYDSFDL-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium succinimide 、 (S)-5-(2-Mesyloxyethyl)-2,2-dimethyl[1,3]dioxolan-4-one 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-1-[2-(2,2-Dimethyl-5-oxo[1,3]dioxolan-4-yl)-ethyl]-pyrrolidine2,5-dione
  参考文献：
  名称：

  Mercaptoacyl matrix metalloproteinase inhibitors: The effect of substitution at the mercaptoacyl moiety

  摘要：

  The in vitro potency of orally-active mercaptoacyl matrix metalloproteinase inhibitors is increased by the introduction of appropriate substituents on the mercaptoacyl moiety. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10069-5
• 作为产物：
  描述：

  甲基磺酰氯 、 (S)-5-(2-羟基乙基)-2,2-二甲基-1,3-二噁烷-4-酮 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以77.7%的产率得到(S)-5-(2-Mesyloxyethyl)-2,2-dimethyl[1,3]dioxolan-4-one
  参考文献：
  名称：

  EP2230239

  摘要：

  公开号：

文献信息

• Selective MMP inhibitors having reduced side-effects
  申请人：——

  公开号：US20020035065A1

  公开（公告）日：2002-03-21

  The subject invention pertains to matrix metalloproteinase (MMP) inhibitors that exhibit an IC 50 of below 10 −4 M against MMP and have substantially no activity against non-MMP metalloproteinase-related events. The MMP inhibitors of the invention have reduced side-effects, especially with respect to joint pain.

  本发明涉及一种针对基质金属蛋白酶（MMP）的抑制剂，其对MMP的IC50低于10^-4M，并且几乎不对非MMP金属蛋白酶相关事件产生活性。本发明的MMP抑制剂具有减少的副作用，尤其是关节疼痛方面。
• [EN] SELECTIVE MMP INHIBITORS HAVING REDUCED SIDE-EFFECTS<br/>[FR] INHIBITEURS SELECTIFS DE LA METALLOPROTEASE MATRICIELLE PRESENTANT DES EFFETS SECONDAIRES REDUITS
  申请人：DARWIN DISCOVERY LIMITED

  公开号：WO1998039024A1

  公开（公告）日：1998-09-11

  (EN) A matrix metalloproteinase (MMP) inhibitor that exhibits an IC50 of below 10-4M against MMP and has substantially no activity against non-MMP metalloproteinase-related events has reduced side-effects, especially with respect to joint pain.(FR) L'invention concerne un inhibiteur de la métalloprotéase matricielle qui présente une concentration inhibitrice 50 de moins de 10-4M contre la métalloprotéase matricielle, et n'exerce sensiblement aucune activité contre les évènements non liés à la métalloprotéase matricielle. Cet inhibiteur présente des effets secondaires réduits, en particulier, dans le domaine des douleurs articulaires.

  一种基质金属蛋白酶（MMP）抑制剂，对MMP的IC50低于10-4M，并且几乎没有对非MMP金属蛋白酶相关事件的活性，具有减少副作用的作用，尤其是对关节疼痛方面的作用。
• EP2230239
  申请人：——

  公开号：——

  公开（公告）日：——
• SELECTIVE MMP INHIBITORS HAVING REDUCED SIDE-EFFECTS
  申请人：Darwin Discovery Limited

  公开号：EP0981366B1

  公开（公告）日：2004-01-21
• Method for Preparing 4-[9-(6-Aminopurine)]-2-(S)-Hydroxyl-Butyric Acid Methyl Ester
  申请人：Nan Fajun

  公开号：US20110201810A1

  公开（公告）日：2011-08-18

  The present invention discloses a novel method for preparing and purifying 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester. The preparation started from cheap and easily available L-malic acid, which was transformed to intermediate I after simultaneous protection of the groups of 1-carboxyl and 2-hydroxyl. The intermediate I was selectively reduced to intermediate alcohol II, whose hydroxyl group was further transformed to an easily leaving group to afford intermediate III. The intermediate III was nucleophilically substituted with adenine to afford intermediate IV. The intermediate IV was deprotected and methyl-esterified simultaneously in methanol in the presence of an acid or a base to afford crude 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester, which was purified by recrystallization to afford the purified product. Comparing with the prior preparation methods, the present method has advantages in low cost, mild conditions, high retention of the chiral center during the reaction, high productivity, great improvement in the quality and yield of the product and great decrease in cost, and thus is suitable for the production on a large scale.