(2R,3R)-(3-hydroxymethyl-1,4-dioxa-spiro[4.4]non-2-yl)-methanol | 33496-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-(3-hydroxymethyl-1,4-dioxa-spiro[4.4]non-2-yl)-methanol
• 英文别名: 2,3-O-cyclopentylidene-D-threitol；[(2R,3R)-3-(hydroxymethyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methanol
• CAS: 33496-85-4
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: ZNMWHPGEUHDVNY-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-(3-hydroxymethyl-1,4-dioxa-spiro[4.4]non-2-yl)-methanol 在 四氮唑 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (2-{Benzyloxy-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-ylmethoxy]-phosphanyloxy}-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)

  摘要：

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.

  DOI：

  10.1021/jo011185a
• 作为产物：
  描述：

  (2S,3S)-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid diethyl ester 以61%的产率得到(2R,3R)-(3-hydroxymethyl-1,4-dioxa-spiro[4.4]non-2-yl)-methanol
  参考文献：
  名称：

  Platinum(II) complex and processes for preparing the same

  摘要：

  本文披露了具有强效抗肿瘤活性的新型铂（II）配合物，其化学式为（1），其中R.sub.1和R.sub.2，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与连接的碳原子共同形成环烷基基团；两个X共同形成由化学式（a）或（b）表示的基团，其中，R.sub.3为氢原子或甲基基团；R.sub.4和R.sub.5，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与碳原子共同形成环丁烷基团；以及4,5-双(氨甲基)-1,3-二氧杂环戊烷基团中各立体中心的绝对构型为（4R,5R）或（4S,5S）；制备这些配合物的方法；以及它们用于治疗动物或人类癌症的用途。此外，本文还披露了用于制备铂（II）配合物的新型中间体以及制备这些中间体的方法。

  公开号：

  US05395947A1

文献信息

• Platinum(II) complex and processes for preparing the same
  申请人：Sunkyong Industries, Ltd.

  公开号：US05395947A1

  公开（公告）日：1995-03-07

  Disclosed herein are novel platinum(II) complexes having a potent anti-tumor activity which are represented by the formula (1), ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom or a C.sub.1-4 alkyl group, respectively, or jointly form a cycloalkane group together with the carbon atom attached thereto; two Xs jointly form a group represented by formula (a) or (b) wherein, R.sub.3 is a hydrogen atom or a methyl group; R.sub.4 and R.sub.5, which may be the same or different, are a hydrogen atom or a C.sub.1-4 alkyl group, respectively, or jointly form a cyclobutane together with the carbon thereto; and the absolute configurations at the respective chiral centers in the 4,5-bis(aminomethyl)-1,3-dioxolane moiety are (4R,5R) or (4S,5S); processes for the preparing the same; and their use for treating animal or human cancer. Further, disclosed herein are novel intermediates useful for the preparation of the platinum(II) complexes and processes for preparing said intermediates.

  本文披露了具有强效抗肿瘤活性的新型铂（II）配合物，其化学式为（1），其中R.sub.1和R.sub.2，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与连接的碳原子共同形成环烷基基团；两个X共同形成由化学式（a）或（b）表示的基团，其中，R.sub.3为氢原子或甲基基团；R.sub.4和R.sub.5，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与碳原子共同形成环丁烷基团；以及4,5-双(氨甲基)-1,3-二氧杂环戊烷基团中各立体中心的绝对构型为（4R,5R）或（4S,5S）；制备这些配合物的方法；以及它们用于治疗动物或人类癌症的用途。此外，本文还披露了用于制备铂（II）配合物的新型中间体以及制备这些中间体的方法。
• Hybrid phosphoinositide phospholipids: compositions and uses
  申请人：Prestwich Glenn

  公开号：US20050148042A1

  公开（公告）日：2005-07-07

  The methods and compositions disclosed herein concern the synthesis of a novel class of “two-headed” phospholipid-phosphoinositide hybrids possessing a carbon backbone, such as 2,3-diacylthreitol, erythritol or a synthetic module. The second phospholipid head group allows introduction of a biochemical or chemical moiety in a position orthogonal in space to those occupied by the phosphoinositide head group and the two acyl chains. The diacyl moieties allow for the incorporation of Pea-PIP 2 into a lipid bilayer, while the Ptdlns(4,5)P 2 moiety in the aqueous layer is specifically recognized by lipid binding proteins. In alternative embodiments of the invention, reporters, for example biotin, fluorophores and/or spin labels, are attached to the free amino group of the head groups of such molecules to specifically target the reporters to the lipid-water interface.

  本文所披露的方法和组合物涉及合成一种新型的“双头”磷脂酰肌醇酰杂交物，具有碳骨架，例如2,3-二酰基己二醇、赤藓糖或合成模块。第二个磷脂酰头基允许在空间上与磷脂酰肌醇头基和两个酰基链所占据的位置相垂直引入生化或化学基团。二酰基基团允许将豌豆-PIP2并入脂质双层，而水相层中的Ptdlns（4,5）P2基团则被脂质结合蛋白特异性识别。在发明的其他实施方式中，例如生物素、荧光染料和/或自旋标记，附加在此类分子头基的自由氨基上，以特异性地将报告物靶向到脂质-水界面。
• NOVEL PLATINUM(II) COMPLEX AND PROCESSES FOR PREPARING THE SAME
  申请人：SUNKYONG INDUSTRIES LTD.

  公开号：EP0586378B1

  公开（公告）日：1998-09-23
• US5395947A
  申请人：——

  公开号：US5395947A

  公开（公告）日：1995-03-07
• [EN] NOVEL PLATINUM(II) COMPLEX AND PROCESSES FOR PREPARING THE SAME
  申请人：——

  公开号：WO1992016539A1

  公开（公告）日：1992-10-01

  [EN] Disclosed herein are novel platinum(II) complexe having a potent anti-tumor activity which are represented by formula (1), wherein R1 and R2, which may be the same or different, are a hydrogen atom or a C1-4 alkyl group, respectively, or jointly form a cycloalkane group together with the carbon atom attached thereto; two Xs jointly form a group represented by formula (a) or (b) wherein, R3 is a hydrogen atom or a methyl group; R4 and R5, which may be the same or different, are a hydrogen atom or a C1-4 alkyl group, respectively, or jointly form a cyclobutane together with the carbon thereto; and the absolute configurations at the respective chiral centers in the 4,5-bis(aminomethyl)-1,3-dioxolane moiety are (4R, 5R) or (4S, 5S); processes for preparing the same; and their use for treating animal or human cancer. Further, disclosed herein are novel intermediates useful for the preparation of the platinum(II) complexes and processes for preparing said intermediates.
  [FR] Nouveaux complexes de platine (II) présentant une puissante activité antitumorale et répondant à la formule (I), dans laquelle R1 et R2 sont identiques ou différents et représentent un atome d'hydrogène ou un groupe alkyle C1-4 respectivement, ou forment ensemble un groupe cycloalcane conjointement avec l'atome de carbone lié à celui-ci; les deux X forment ensemble un groupe répondant à la formule (a) ou (b), dans laquelle R3 représente un atome d'hydrogène ou un groupe méthyle; R4 et R5 sont identiques ou différents et représentent un atome d'hydrogène ou un groupe alkyle C1-4 respectivement, ou forment ensemble un cyclobutane conjointement avec l'atome de carbone lié à celui-ci; et les configurations absolues au niveau des centres chiraux respectifs dans la fraction 4,5-bis(aminométhyl)-1,3-dioxolane sont (4R, 5R) ou (4S), (5S); leurs procédés de préparation; et leur utilisation pour le traitement des cancers chez l'homme et chez les animaux. Par ailleurs, on décrit de nouveaux intermédiaires utilisés pour préparer lesdits complexes de platine (II), ainsi que des procédés de préparation de ces intermédiaires.