(3aR,4S,5S,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aR,4S,5S,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde
• 化学式: C₁₄H₂₄O₄Si
• 分子量: 284.42
• InChiKey: CLCQNBJFWQERSS-RHYQMDGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4S,5S,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde 以93的产率得到(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  NOVEL PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND INTERMEDIATES THEREOF

  摘要：

  本发明涉及一种新型的制备具有式（K）的前列腺素化合物的方法，其中R选自以下组中的一种：C1-C7烷基；C7-C17芳基烷基，其中芳基基团未取代或取代有1至3个取代基，所述取代基选自C1-C6烷基，卤素和CF3；以及（CH2）nOR2，其中n为1至3，R2代表未取代或取代有1至3个取代基的C6-C10芳基基团，所述取代基选自C1-C6烷基，卤素和CF3；R1选自OR3和NHR3，其中R3为C1-C6烷基，H；虚线表示双键或单键。本发明还公开了新型中间体。

  公开号：

  US20120209011A1

文献信息

• [EN] PROCESS FOR THE PREPARATION OF F-SERIES PROSTAGLANDINS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE PROSTAGLANDINES DE LA SÉRIE F
  申请人：CAYMAN CHEM CO

  公开号：WO2011046569A1

  公开（公告）日：2011-04-21

  A process for the synthesis and purification of F-series prostaglandin compounds and synthetic intermediates used to prepare them. The synthetic intermediates are solid and may be purified by precipitation and therefore may form the representative F-series prostaglandin compounds such as latanoprost, bimatoprost, fluprostenol, cloprostenol, and substituted analogs therefrom in highly pure forms.

  一种合成和纯化F系列前列腺素化合物及其合成中间体的方法。这些合成中间体是固体并且可以通过沉淀纯化，因此可以形成高纯度的代表性F系列前列腺素化合物，如拉坦前列素，比马前列素，氟前列醇，克罗前列醇和其取代类似物。
• Process for the preparation of F-series prostaglandins
  申请人：Chambournier Gilles

  公开号：US08901319B2

  公开（公告）日：2014-12-02

  A process for the synthesis and purification of F-series prostaglandin compounds and synthetic intermediates used to prepare them. The synthetic intermediates are solid and may be purified by precipitation and therefore may form the representative F-series prostaglandin compounds such as latanoprost, bimatoprost, fluprostenol, cloprostenol, and substituted analogs therefrom in highly pure forms.

  一种用于合成和纯化F系列前列腺素化合物及用于制备它们的合成中间体的过程。这些合成中间体是固体，可以通过沉淀纯化，因此可以形成代表性的F系列前列腺素化合物，如拉坦前列素、比马前列素、氟前列醇、氯前列素和其取代类似物，以高度纯净的形式。
• [EN] NOVEL PROCESSES FOR THE PREPARATION OF PROSTAGLANDIN AMIDES<br/>[FR] NOUVEAU PROCÉDÉ POUR LA PRÉPARATION D'AMIDES DE PROSTAGLANDINES
  申请人：CHINOIN ZRT

  公开号：WO2012164324A1

  公开（公告）日：2012-12-06

  The subject of the invention is process for the preparation of the prostaglandin amides of the general formula I, - where in the formula the bonds marked with dotted lines may be single or double bonds, in the case of double bounds at positions 5,6 and 13,14 they may be in cis or in trans orientation, Q stands for a hydroxyl-group and Z stands for a hydroxyl- or oxo-group, R1 and R2 independently represent hydrogen atom or a straight or branched C1-10 alkyl- or aralkyl- group, optionally substituted with -ONO2 group, or an aralkyl- or aryl- group, which contains heteroatom, R3 represents a straight or branched, saturated or unsaturated C4-6 hydrocarbon group, or a C4-10 alkylcycloalkyl- or cycloalkyl- group, or an optionally with alkyl group or halogen atom substituted phenyl-, C7-10 alkylaryl- or hetaryl- group, Y represents (CH2)n group or 0 atom or S atom, and where n=0-3.

  本发明的主题是一种制备通式I的前列腺素酰胺的方法，其中在该式中，用虚线标记的键可以是单键或双键，在位置5,6和13,14处的双键可以是顺式或反式的，Q代表羟基，Z代表羟基或氧基，R1和R2分别代表氢原子或直链或支链C1-10烷基或芳基烷基，可选地取代-ONO2基团，或含有杂原子的芳基烷基或芳基基团，R3代表直链或支链、饱和或不饱和的C4-6烃基，或C4-10烷基环烷基或环烷基基团，或可选地用烷基或卤原子取代的苯基、C7-10烷基芳基基团或杂芳基基团，Y代表(CH2)n基团、0原子或S原子，其中n=0-3。
• PROCESS FOR THE PREPARATION OF PROSTAGLANDIN DERIVATIVES
  申请人：Biffi Giancarlo

  公开号：US20120016136A1

  公开（公告）日：2012-01-19

  The invention concerns a new process for the preparation of prostaglandin derivatives, in particular prostaglandin F 2α derivatives, for example bimatoprost, latanoprost and travoprost, the new intermediates of said process and their use in the preparation of prostagblandin derivatives.

  本发明涉及一种制备前列腺素衍生物的新工艺，特别是前列腺素F2α衍生物，例如比马前列素、拉坦前列素和曲前列素，该工艺的新中间体及其在制备前列腺素衍生物中的应用。
• NOVEL PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND INTERMEDIATES THEREOF
  申请人：Aswathanarayanappa Chandrashekar

  公开号：US20120209011A1

  公开（公告）日：2012-08-16

  This invention relates to novel process for the preparation of prostaglandin compounds having formula (K), wherein R is selected from the group consisting of C 1 -C 7 alkyl; C 7 -C 17 aralkyl wherein the aryl group is unsubstituted or substituted with one to three substituents selected from the group consisting of C 1 -C 6 alkyl, halo and CF 3 ; and (CH 2 ) n OR 2 wherein n is from 1 to 3 and R 2 represents a C 6 -C 10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C 1 -C 6 alkyl, halo and CF 3 ; and R 1 is selected from OR 3 and NHR 3 wherein R 3 is C 1 -C 6 alkyl, H; and dashed lines represents a double bond or a single bond, is disclosed. Novel intermediates are also disclosed.

  本发明涉及一种新型的制备具有式（K）的前列腺素化合物的方法，其中R选自以下组中的一种：C1-C7烷基；C7-C17芳基烷基，其中芳基基团未取代或取代有1至3个取代基，所述取代基选自C1-C6烷基，卤素和CF3；以及（CH2）nOR2，其中n为1至3，R2代表未取代或取代有1至3个取代基的C6-C10芳基基团，所述取代基选自C1-C6烷基，卤素和CF3；R1选自OR3和NHR3，其中R3为C1-C6烷基，H；虚线表示双键或单键。本发明还公开了新型中间体。