(1S,2S,3S,7R,8R)-8-deuterio-2,3,7-trihydroxy-3-methyl-8-(morpholin-4-ylmethyl)-11-oxa-5,13-diazatricyclo[5.4.2.01,5]tridecane-6,12-dione | 143063-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (1S,2S,3S,7R,8R)-8-deuterio-2,3,7-trihydroxy-3-methyl-8-(morpholin-4-ylmethyl)-11-oxa-5,13-diazatricyclo[5.4.2.01,5]tridecane-6,12-dione
• CAS: 143063-25-6
• 化学式: C₁₆H₂₅N₃O₇
• 分子量: 372.382
• InChiKey: ONZJRLJACZJKSH-BLMISJJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  二环霉素 在 吡啶 、 重水 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 (1S,2S,3S,7R,8R)-8-deuterio-2,3,7-trihydroxy-3-methyl-8-(morpholin-4-ylmethyl)-11-oxa-5,13-diazatricyclo[5.4.2.01,5]tridecane-6,12-dione
  参考文献：
  名称：

  The synthesis and reactivity of [N(8)-C(3')]-cyclized bicyclomycin. Evidence of the role of the C(1)-triol group in bicyclomycin-mediated processes

  摘要：

  The C(1) triol group in the antibiotic, bicyclomycin (1) has been proposed to play an integral role in the bonding of key protein nucleophiles to the distal C(5)-C(5a) terminal double bond in the drug. Evidence in support of this concept has been provided by the comparison of the reactivities of bicyclomycin (1), the [N(8)-C(3')]-cyclized bicyclomycin adduct 3, 2',3'-bicyclomycin acetonide (17), and the acetonide derivative of 3, 18, with sodium ethanethiolate. Significantly, 3 displayed enhanced reactivity versus 1, 17, and 18 in this transformation. The controlling factors for the increased reactivity of 3 have been discerned and the importance of the C(1') hydroxyl group delineated. Key kinetic parameters are reported for the treatment of both 3 and 17 with 2-mercaptopyridine. Structural details are provided for both C(5a) thiolate and amine adducts of 3. The importance of these findings in relation to the mode of action of bicyclomycin are briefly discussed.

  DOI：

  10.1021/jo00045a041