(2S,3S)-3-Benzyloxy-2-benzyloxymethyl-2,3-dihydro-thiophene | 286013-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-3-Benzyloxy-2-benzyloxymethyl-2,3-dihydro-thiophene
• 英文别名: (2S,3S)-3-phenylmethoxy-2-(phenylmethoxymethyl)-2,3-dihydrothiophene
• CAS: 286013-41-0
• 化学式: C₁₉H₂₀O₂S
• 分子量: 312.433
• InChiKey: BBIDJCQWMKQAMM-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Benzyloxy-2-benzyloxymethyl-2,3-dihydro-thiophene 在 偶氮二异丁腈 、 三正丁基氢锡 、 一氯化碘 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 1-((2S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-ethyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 4-thiofuranoid 1,2-glycals and their application to stereoselective synthesis of 4′-thionucleosides

  摘要：

  Convenient one-pot procedures using iodine monochloride have been developed for the preparation of two 4-thio-1,2-glycals from readily available starting materials and for their beta-anomer selective conversion into 2'-iodo-4'-thionucleosides. Conditions for the reductive de-iodination of these iodonucleosides have been established and hence routes to a range of 2'-deoxy-4'-thionucleosides become feasible. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00366-x
• 作为产物：
  描述：

  3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S)-3-Benzyloxy-2-benzyloxymethyl-2,3-dihydro-thiophene
  参考文献：
  名称：

  Synthesis of 4-thiofuranoid 1,2-glycals and their application to stereoselective synthesis of 4′-thionucleosides

  摘要：

  Convenient one-pot procedures using iodine monochloride have been developed for the preparation of two 4-thio-1,2-glycals from readily available starting materials and for their beta-anomer selective conversion into 2'-iodo-4'-thionucleosides. Conditions for the reductive de-iodination of these iodonucleosides have been established and hence routes to a range of 2'-deoxy-4'-thionucleosides become feasible. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00366-x