(2S,3S,4R)-3-benzyloxy-4-((1R/S)-(1-ethoxy)-ethoxy)-2-(iodomethyl)tetrahydrofuran | 373646-85-6

• 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,4R)-3-benzyloxy-4-((1R/S)-(1-ethoxy)-ethoxy)-2-(iodomethyl)tetrahydrofuran
• CAS: 373646-85-6
• 化学式: C₁₆H₂₃IO₄
• 分子量: 406.261
• InChiKey: QJZXOBOYIKATPK-SJFVDLKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-3-benzyloxy-4-((1R/S)-(1-ethoxy)-ethoxy)-2-(iodomethyl)tetrahydrofuran 在 吡啶 、 18-冠醚-6 、 potassium oxide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.52h， 生成 (3R,4R,5R)-5-[(benzyloxy)methyl]-4-(benzyloxy)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of 1,4-anhydro-alditols, 1,4-anhydro-2-amino-alditols and d- and l-isonucleosides from 2,3-O-isopropylidene-d-glyceraldehyde using iodine-induced cyclization as the key step

  摘要：

  We have stereoselectively prepared the enantiomeric 1,4-anhydro-alditols (-)-15 and (+)-15, 1,4-anhydro-2-amino-alditols (-)-19 and (+)-19, and isonucleosides (-)-22, (+)-22 and 25, from 2,3-O-isopropylidene-D-glyceraldehyde. The key step was the iodine-induced cyclization of 4-pentene-1,2,3-triols 2 and 3 to give, respectively, the tetrahydrofuran derivatives 4 and 5. In these compounds we have optimized the substitution of iodine for oxygen-bearing groups. Results were best when we used potassium superoxide as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00283-x
• 作为产物：
  描述：

  乙烯基乙醚 、 (2S,3R,4R)-3-benzyloxy-2-iodomethyltetrahydrofuran-4-ol 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到(2S,3S,4R)-3-benzyloxy-4-((1R/S)-(1-ethoxy)-ethoxy)-2-(iodomethyl)tetrahydrofuran
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of 1,4-anhydro-alditols, 1,4-anhydro-2-amino-alditols and d- and l-isonucleosides from 2,3-O-isopropylidene-d-glyceraldehyde using iodine-induced cyclization as the key step

  摘要：

  We have stereoselectively prepared the enantiomeric 1,4-anhydro-alditols (-)-15 and (+)-15, 1,4-anhydro-2-amino-alditols (-)-19 and (+)-19, and isonucleosides (-)-22, (+)-22 and 25, from 2,3-O-isopropylidene-D-glyceraldehyde. The key step was the iodine-induced cyclization of 4-pentene-1,2,3-triols 2 and 3 to give, respectively, the tetrahydrofuran derivatives 4 and 5. In these compounds we have optimized the substitution of iodine for oxygen-bearing groups. Results were best when we used potassium superoxide as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00283-x