(S)-4-(benzyloxy)-1-((4S,5S)-5-(benzyloxymethyl)-2,2-di-methyl-1,3-dioxolan-4-yl)but-2-yn-1-ol | 1239477-12-3

• 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: (S)-4-(benzyloxy)-1-((4S,5S)-5-(benzyloxymethyl)-2,2-di-methyl-1,3-dioxolan-4-yl)but-2-yn-1-ol
• 英文别名: (1S)-1-[(4S,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-4-phenylmethoxybut-2-yn-1-ol
• CAS: 1239477-12-3
• 化学式: C₂₄H₂₈O₅
• 分子量: 396.483
• InChiKey: NJTSIEDASNIWSX-VABKMULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苄基丙炔基醚 、 (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 在 正丁基锂 、 titanium(IV) isopropylate 、 四氯化钛 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 (R)-4-(benzyloxy)-1-((4S,5S)-5-(benzyloxymethyl)-2,2-di-methyl-1,3-dioxolan-4-yl)but-2-yn-1-ol 、 (S)-4-(benzyloxy)-1-((4S,5S)-5-(benzyloxymethyl)-2,2-di-methyl-1,3-dioxolan-4-yl)but-2-yn-1-ol
  参考文献：
  名称：

  Diastereoselective synthesis of propargylic fluorides and its application in preparation of monofluorinated sugar

  摘要：

  An effective method to diastereoselectively synthesize enantioenriched propargylic fluorides was developed via S(N)1 type reaction of DAST participated dehydroxy-fluorination of diastereomeric propargylic alcohol cobalt carbonyl complexes. A serious of propargylic fluorides can be prepared by this approach in good yields with moderate to high diastereoselectivities. To demonstrate the application of this approach in synthesis, monofluorinated sugar 12, an important and versatile building block, was prepared in an efficient manner. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.078

文献信息

• Diastereoselective synthesis of propargylic fluorides and its application in preparation of monofluorinated sugar
  作者：Shilu Fan、Chun-Yang He、Xingang Zhang

  DOI：10.1016/j.tet.2010.04.078

  日期：2010.7

  An effective method to diastereoselectively synthesize enantioenriched propargylic fluorides was developed via S(N)1 type reaction of DAST participated dehydroxy-fluorination of diastereomeric propargylic alcohol cobalt carbonyl complexes. A serious of propargylic fluorides can be prepared by this approach in good yields with moderate to high diastereoselectivities. To demonstrate the application of this approach in synthesis, monofluorinated sugar 12, an important and versatile building block, was prepared in an efficient manner. (C) 2010 Elsevier Ltd. All rights reserved.