(2S)-3-苄氧基-2-羟丙基三氟甲磺酸酯 | 1026378-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2S)-3-苄氧基-2-羟丙基三氟甲磺酸酯
• 英文名称: (2S)-3-benzyloxy-2-hydroxypropyl trifluoromethanesulfonate
• 英文别名: [(2S)-2-hydroxy-3-phenylmethoxypropyl] trifluoromethanesulfonate
• CAS: 1026378-85-7
• 化学式: C₁₁H₁₃F₃O₅S
• 分子量: 314.282
• InChiKey: XVGUZZRTKCDJCB-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-3-苄氧基-2-羟丙基三氟甲磺酸酯 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.42h， 生成 3-[(2R)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(benzyloxy)-2-(tert-butyldimethylsilyloxy)propane
  参考文献：
  名称：

  Facile Route to 3,5-Disubstituted Morpholines:  Enantioselective Synthesis of O-Protected trans-3,5-Bis(hydroxymethyl)morpholines

  摘要：

  trans-3,5-Bis(benzyl/tert-butyldiphenylsilyloxymethyl)morpholines, promising candidates for the C-2-symmetric class of chiral reagents, were prepared with excellent optical purity. A key step in the synthesis is the coupling of a serinol derivative with 2,3-O-isopropylideneglycerol triflate or its equivalent. This methodology was extended to the synthesis of chiral trans-3-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxymethyl)morpholine, a potentially useful chiral building block.

  DOI：

  10.1021/ol035998s
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (R)-(+)-3-苄氧基-1,2-丙二醇 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (2S)-3-苄氧基-2-羟丙基三氟甲磺酸酯
  参考文献：
  名称：

  Facile Route to 3,5-Disubstituted Morpholines:  Enantioselective Synthesis of O-Protected trans-3,5-Bis(hydroxymethyl)morpholines

  摘要：

  trans-3,5-Bis(benzyl/tert-butyldiphenylsilyloxymethyl)morpholines, promising candidates for the C-2-symmetric class of chiral reagents, were prepared with excellent optical purity. A key step in the synthesis is the coupling of a serinol derivative with 2,3-O-isopropylideneglycerol triflate or its equivalent. This methodology was extended to the synthesis of chiral trans-3-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxymethyl)morpholine, a potentially useful chiral building block.

  DOI：

  10.1021/ol035998s

文献信息

• Facile Route to 3,5-Disubstituted Morpholines:  Enantioselective Synthesis of O-Protected <i>trans</i>-3,5-Bis(hydroxymethyl)morpholines
  作者：Rajesh Dave、N. André Sasaki

  DOI：10.1021/ol035998s

  日期：2004.1.1

  trans-3,5-Bis(benzyl/tert-butyldiphenylsilyloxymethyl)morpholines, promising candidates for the C-2-symmetric class of chiral reagents, were prepared with excellent optical purity. A key step in the synthesis is the coupling of a serinol derivative with 2,3-O-isopropylideneglycerol triflate or its equivalent. This methodology was extended to the synthesis of chiral trans-3-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxymethyl)morpholine, a potentially useful chiral building block.