(2R,3S)-2-Hydroxymethyl-5-phenylselanyl-tetrahydro-furan-3-ol | 659720-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-2-Hydroxymethyl-5-phenylselanyl-tetrahydro-furan-3-ol
• CAS: 659720-30-6
• 化学式: C₁₁H₁₄O₃Se
• 分子量: 273.19
• InChiKey: AZLKFBYDVIPCLQ-MTULOOOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.52
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-Hydroxymethyl-5-phenylselanyl-tetrahydro-furan-3-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,4-anhydro-2-deoxy-3,5-di-O-pivaloyl-D-erythro-pent-1-enitol
  参考文献：
  名称：

  Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl–carbohydrate derivatives

  摘要：

  Differently protected erythro and threo furanoid glycals were synthesized by selenoxide elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions ((BuOOH)-Bu-i, Ti((OPr)-Pr-i)(4), (Et2PrN)-Pr-i). The phenyl 1-selenoglycosides were obtained from methyl 2-deoxy-D-erythro-pentofuranoside by protection of the primary hydroxyl or both hydroxyls and further reaction with PhSeH in the presence of BF3. Et2O. Erythro and threo furanoid glycals were also prepared by treating 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols under similar conditions. The 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols were obtained from 4-pentene-1,2,3-triols by a 5-endo selenium electrophilic induced cyclization. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00256-7
• 作为产物：
  描述：

  甲基-2-脱氧-D-核糖 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S)-2-Hydroxymethyl-5-phenylselanyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl–carbohydrate derivatives

  摘要：

  Differently protected erythro and threo furanoid glycals were synthesized by selenoxide elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions ((BuOOH)-Bu-i, Ti((OPr)-Pr-i)(4), (Et2PrN)-Pr-i). The phenyl 1-selenoglycosides were obtained from methyl 2-deoxy-D-erythro-pentofuranoside by protection of the primary hydroxyl or both hydroxyls and further reaction with PhSeH in the presence of BF3. Et2O. Erythro and threo furanoid glycals were also prepared by treating 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols under similar conditions. The 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols were obtained from 4-pentene-1,2,3-triols by a 5-endo selenium electrophilic induced cyclization. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00256-7