2,2-dimethyl-N-[9-[(1S,3R,4R,5R)-4-triethylsilyloxy-1-(triethylsilyloxymethyl)-2,6-dioxabicyclo[3.1.0]hexan-3-yl]purin-6-yl]propanamide | 877466-03-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2,2-dimethyl-N-[9-[(1S,3R,4R,5R)-4-triethylsilyloxy-1-(triethylsilyloxymethyl)-2,6-dioxabicyclo[3.1.0]hexan-3-yl]purin-6-yl]propanamide
• CAS: 877466-03-0
• 化学式: C₂₇H₄₇N₅O₅Si₂
• 分子量: 577.872
• InChiKey: MIYKCBLKWRVYJZ-LGIRTZQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-N-[9-[(1S,3R,4R,5R)-4-triethylsilyloxy-1-(triethylsilyloxymethyl)-2,6-dioxabicyclo[3.1.0]hexan-3-yl]purin-6-yl]propanamide 、 三甲基铝 以 二氯甲烷 为溶剂， 生成 9-[2,5-bis-O-(triethylsilyl)-4-C-methyl-β-D-xylofuranosyl]-N⁶-pivaloyladenine 、 9-[2,5-bis-O-(triethylsilyl)-4-C-methyl-β-L-arabinofuranosyl]-N⁶-pivaloyladenine
  参考文献：
  名称：

  环氧糖核苷的合成用途。

  摘要：

  描述了核苷的1'，2'-，3'，4'-和4'，5'-环氧衍生物的制备及其在1'-和4'-支链类似物的立体选择性合成中的用途。

  DOI：

  10.1080/15257770701489979
• 作为产物：
  描述：

  3'-deoxy-3',4'-didehydroadenosine 在 吡啶 、 二甲基二环氧乙烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 26.5h， 生成 2,2-dimethyl-N-[9-[(1S,3R,4R,5R)-4-triethylsilyloxy-1-(triethylsilyloxymethyl)-2,6-dioxabicyclo[3.1.0]hexan-3-yl]purin-6-yl]propanamide
  参考文献：
  名称：

  Anti versus Syn Opening of Epoxides Derived from 9-(3-Deoxy-β-d-glycero-pent-3-enofuranosyl)adenine with Me₃Al:  Factors Controlling the Stereoselectivity

  摘要：

  [graphics]Upon epoxidation with dimethyldioxirane, the 2',5'-bis-O-silyl derivatives of 9-(3-deoXy-beta-D-glyceropent-3-enofuranosyl)adenine gave the respective "3',4'-up" epoxides exclusively. Reaction between these epoxides and Me3Al was investigated in detail. It was found that the stereoselectivity of epoxide ring opening (anti versus syn) varied significantly upon changing the amount of Me3Al, the solvent, the O-silyl protecting group, and the reaction temperature. A possible reaction mechanism is proposed.

  DOI：

  10.1021/jo052243l

文献信息

• Synthetic Use Of Epoxy-Sugar Nucleosides
  作者：Hiromichi Tanaka、Yutaka Kubota、Shingo Takeda、Kazuhiro Haraguchi

  DOI：10.1080/15257770701489979

  日期：2007.11.26

  Preparation of 1',2 '-, 3 ',4 '-, and 4 ',5 '-epoxy derivatives of nucleosides and their use for the stereoselective synthesis of 1'- and 4 '-branched analogues are described.

  描述了核苷的1'，2'-，3'，4'-和4'，5'-环氧衍生物的制备及其在1'-和4'-支链类似物的立体选择性合成中的用途。
• Anti versus Syn Opening of Epoxides Derived from 9-(3-Deoxy-β-<scp>d</scp>-<i>g</i><i>lycero</i>-pent-3-enofuranosyl)adenine with Me₃Al:  Factors Controlling the Stereoselectivity
  作者：Yutaka Kubota、Kazuhiro Haraguchi、Mayumi Kunikata、Mari Hayashi、Masaomi Ohkawa、Hiromichi Tanaka

  DOI：10.1021/jo052243l

  日期：2006.2.1

  [graphics]Upon epoxidation with dimethyldioxirane, the 2',5'-bis-O-silyl derivatives of 9-(3-deoXy-beta-D-glyceropent-3-enofuranosyl)adenine gave the respective "3',4'-up" epoxides exclusively. Reaction between these epoxides and Me3Al was investigated in detail. It was found that the stereoselectivity of epoxide ring opening (anti versus syn) varied significantly upon changing the amount of Me3Al, the solvent, the O-silyl protecting group, and the reaction temperature. A possible reaction mechanism is proposed.