[(2R,3R,4S,5R,6R)-2-(3,3-dimethylpent-4-enoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] 2,2-dimethylpropanoate | 1177257-00-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2R,3R,4S,5R,6R)-2-(3,3-dimethylpent-4-enoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 1177257-00-9
• 化学式: C₃₉H₅₀O₇
• 分子量: 630.822
• InChiKey: QJYPUZPKHIOUKF-SQGINLDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-2-(3,3-dimethylpent-4-enoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] 2,2-dimethylpropanoate 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙腈 为溶剂， 反应 1.75h， 以90%的产率得到2,2-Dimethyl-propionic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  gem-Dimethyl 4-Pentenyl Glycosides: Novel Glycosylating Agents and Anomeric Protecting Groups

  摘要：

  Two classes of gem-dimethyl 4-n-pentenyl glycosides (i.e., C2-series and C3-series) have been prepared and studied in both the glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. These novel glycosylating agents, which are analogues of Fraser-Reid's 4-n-penterryl glycosyl donors, show increased reactivity in side-by-side studies by virtue of the gem-dimethyl effect.

  DOI：

  10.1021/ol901313z
• 作为产物：
  描述：

  、 三甲基乙酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 [(2R,3R,4S,5R,6R)-2-(3,3-dimethylpent-4-enoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  gem-Dimethyl 4-Pentenyl Glycosides: Novel Glycosylating Agents and Anomeric Protecting Groups

  摘要：

  Two classes of gem-dimethyl 4-n-pentenyl glycosides (i.e., C2-series and C3-series) have been prepared and studied in both the glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. These novel glycosylating agents, which are analogues of Fraser-Reid's 4-n-penterryl glycosyl donors, show increased reactivity in side-by-side studies by virtue of the gem-dimethyl effect.

  DOI：

  10.1021/ol901313z

文献信息

• <i>gem-</i>Dimethyl 4-Pentenyl Glycosides: Novel Glycosylating Agents and Anomeric Protecting Groups
  作者：Michael Fortin、Justin Kaplan、Khoa Pham、Sharon Kirk、Rodrigo B. Andrade

  DOI：10.1021/ol901313z

  日期：2009.8.20

  Two classes of gem-dimethyl 4-n-pentenyl glycosides (i.e., C2-series and C3-series) have been prepared and studied in both the glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. These novel glycosylating agents, which are analogues of Fraser-Reid's 4-n-penterryl glycosyl donors, show increased reactivity in side-by-side studies by virtue of the gem-dimethyl effect.