9-[3-deoxy-2,5-bis-O-(triethylsilyl)-β-D-glyceropent-3-enofuranosyl]adenine | 877465-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-[3-deoxy-2,5-bis-O-(triethylsilyl)-β-D-glyceropent-3-enofuranosyl]adenine
• 英文别名: 9-[(2R,3R)-3-triethylsilyloxy-5-(triethylsilyloxymethyl)-2,3-dihydrofuran-2-yl]purin-6-amine
• CAS: 877465-93-5
• 化学式: C₂₂H₃₉N₅O₃Si₂
• 分子量: 477.754
• InChiKey: SHTJNJWRVDSGQP-XMSQKQJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-[3-deoxy-2,5-bis-O-(triethylsilyl)-β-D-glyceropent-3-enofuranosyl]adenine 在 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 2.5h， 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
• 作为产物：
  描述：

  3'-deoxy-3',4'-didehydroadenosine 、 三乙基氯硅烷 在 吡啶 作用下， 反应 24.0h， 以100%的产率得到9-[3-deoxy-2,5-bis-O-(triethylsilyl)-β-D-glyceropent-3-enofuranosyl]adenine
  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

• 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.