(2R,3R,3aR,6S,7R,7aR)-7-azido-hexahydro-6-methoxy-2-(phenylthio)-2H-furo[3,2-b]pyran-3-yl pivalate | 828914-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (2R,3R,3aR,6S,7R,7aR)-7-azido-hexahydro-6-methoxy-2-(phenylthio)-2H-furo[3,2-b]pyran-3-yl pivalate
• 英文别名: (2R,3R,3aR,6S,7R,7aR)-7-azido-6-methoxy-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran；[(2R,3R,3aR,6S,7R,7aR)-7-azido-6-methoxy-2-phenylsulfanyl-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyran-3-yl] 2,2-dimethylpropanoate
• CAS: 828914-56-3
• 化学式: C₁₉H₂₅N₃O₅S
• 分子量: 407.491
• InChiKey: KHTFRWSDHHEYRY-HDKMNVHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,3aR,6S,7R,7aR)-7-azido-hexahydro-6-methoxy-2-(phenylthio)-2H-furo[3,2-b]pyran-3-yl pivalate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.17h， 生成 2,2-Dimethyl-propionic acid (2R,3R,3aR,6S,7R,7aR)-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-7-amino-6-methoxy-hexahydro-furo[3,2-b]pyran-3-yl ester
  参考文献：
  名称：

  N-马拉霉素A及其相关双环嘌呤和嘧啶核苷的全合成

  摘要：

  方法双环perhydrofuropyran核苷的全合成被描述为Ñ -analogues所述的天然存在的malayamycin A.形成的Ñ核苷依靠硫代糖苷的激活，经由锍中间体进行。闭环复分解用于两种方法来构建双环二氧杂环杂环。另一种方法依赖于糖前体的使用和环化成双环硫代糖苷。

  DOI：

  10.1021/jo050727b
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 吡啶 、 Grubbs catalyst first generation 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 N-碘代丁二酰亚胺 、 sodium azide 、 水 、 四丁基碘化铵 、 sodium hydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙二醇甲醚 、 N,N-二甲基乙酰胺 、 水 、 mineral oil 为溶剂， 反应 48.0h， 生成 (2R,3R,3aR,6S,7R,7aR)-7-azido-hexahydro-6-methoxy-2-(phenylthio)-2H-furo[3,2-b]pyran-3-yl pivalate
  参考文献：
  名称：

  A Scalable Synthesis of 1-Cytosinyl-N-malayamycin A:  A Potent Fungicide

  摘要：

  A stereocontrolled synthesis of 1-cytosinyl-N-malayamycin A, an N-analogue of the naturally occurring malayamycin A with fungicidal activity, is reported. The approach was designed to rely solely on substrate control for introduction of the required stereochemistry, avoiding the use of chiral reagents or auxiliaries. Formation of the N-nucleoside was achieved through the activation of a thioglycoside, proceeding via sulfonium and thionium intermediates. Ring closure metathesis was used to build the bicyclic perhydrofuropyran heterocycle.

  DOI：

  10.1021/op0600299

文献信息

• Total Synthesis of <i>N</i>-Malayamycin A and Related Bicyclic Purine and Pyrimidine Nucleosides
  作者：Stephen Hanessian、Guobin Huang、Caroline Chenel、Roger Machaalani、Olivier Loiseleur

  DOI：10.1021/jo050727b

  日期：2005.8.1

  synthesis of bicyclic perhydrofuropyran nucleosides as N-analogues of the naturally occurring malayamycin A. Formation of the N-nucleosides relied on the activation of thioglycosides, proceeding via sulfonium intermediates. Ring closure metathesis was used in two approaches to build the bicyclic dioxa heterocycle. Another approach relied on the use of a sugar precursor and cyclization to the bicyclic thioglycoside

  方法双环perhydrofuropyran核苷的全合成被描述为Ñ -analogues所述的天然存在的malayamycin A.形成的Ñ核苷依靠硫代糖苷的激活，经由锍中间体进行。闭环复分解用于两种方法来构建双环二氧杂环杂环。另一种方法依赖于糖前体的使用和环化成双环硫代糖苷。
• [EN] NOVEL 2,7-DIOXO-BICYCLO[4.3.0]NON-5-YL-UREA DERIVATIVES<br/>[FR] NOUVEAUX DERIVES DE 2,7-DIOXO-BICYCLO[4.3.0]NON-5-YL-UREE
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2005005432A1

  公开（公告）日：2005-01-20

  The present invention relates to novel fungicidal 2,7-dioxo-bicyclo[4.3.0] non-5-yl-urea derivatives, to processes for their preparation and to certain intermediate chemicals used in those processes. It also relates to the use of the compounds as biocides, to compositions containing biocidally effective amounts of the compounds and to methods of combating pathogens using the compounds. The invention encompasses 2,7-dioxo-bicyclo[4.3.0]non-5-yl-urea derivatives of formula (I) wherein R is H or C1-6alkyl (for example, methyl), the RO group is cis- or trans- to the NH2CONH group, R1 is H, formyl, C1-8alkylcarbonyl, C3-8cycloalkylcarbonyl, or optionally substituted benzoyl, and X is a N-linked heterocyclic group of the formula (II) or of the formula (III), wherein R2 is H, C1-4alkyl (especially methyl) or halo, or of the formula (IV): The compounds of formula I possess useful plant protecting properties and may advantageously be employed in agricultural practice for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

  本发明涉及新型杀真菌2,7-二氧代双环[4.3.0]戊-5-基脲衍生物，其制备方法以及在这些方法中使用的某些中间化学品。它还涉及将这些化合物用作生物杀菌剂，含有这些化合物生物杀菌有效量的组合物，以及使用这些化合物来对抗病原体的方法。本发明涵盖了公式（I）中R为H或C1-6烷基（例如，甲基），RO基团与NH2CONH基团的位置为顺式或反式，R1为H，甲酰基，C1-8烷基羰基，C3-8环烷基羰基，或者可选择取代的苯甲酰基，X为公式（II）或公式（III）的N-连接杂环基团，其中R2为H，C1-4烷基（尤其是甲基）或卤素，或者为公式（IV）的化合物：公式I的化合物具有有益的植物保护性能，并可有利地用于农业实践中，用于控制或预防植物受植物病原微生物，尤其是真菌的侵害。
• A Scalable Synthesis of 1-Cytosinyl-<i>N</i>-malayamycin A:  A Potent Fungicide
  作者：Olivier Loiseleur、Hermann Schneider、Guobin Huang、Roger Machaalani、Patrice Sellès、Patrick Crowley、Stephen Hanessian

  DOI：10.1021/op0600299

  日期：2006.5.1

  A stereocontrolled synthesis of 1-cytosinyl-N-malayamycin A, an N-analogue of the naturally occurring malayamycin A with fungicidal activity, is reported. The approach was designed to rely solely on substrate control for introduction of the required stereochemistry, avoiding the use of chiral reagents or auxiliaries. Formation of the N-nucleoside was achieved through the activation of a thioglycoside, proceeding via sulfonium and thionium intermediates. Ring closure metathesis was used to build the bicyclic perhydrofuropyran heterocycle.