benzyl N-[(1R)-2-hydroxy-1-[(2S)-6-oxo-2,3-dihydropyran-2-yl]ethyl]carbamate | 1005406-29-0

• 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: benzyl N-[(1R)-2-hydroxy-1-[(2S)-6-oxo-2,3-dihydropyran-2-yl]ethyl]carbamate
• CAS: 1005406-29-0
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: KRXWEXZTLQDCKL-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (6S)-6-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-5,6-dihydropyran-2-one 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到benzyl N-[(1R)-2-hydroxy-1-[(2S)-6-oxo-2,3-dihydropyran-2-yl]ethyl]carbamate
  参考文献：
  名称：

  Trimethylsilyl Trifluoromethanesulfonate (TMSOTf) Assisted Facile Deprotection of N,O-Acetonides

  摘要：

  [GRAPHICS]Employing TMSOTf as an easily available reagent, we have developed a mild and efficient method for the deprotection of both terminal and internal NO-acetonide functionalities. Various regularly used protecting groups and common organic functional moieties were found to be unaffected by the described reaction conditions. In a few representative examples, the present method was also extended to deprotect acetonides obtained from 1,2-, and 1,3-terminal diols. The acetonide deprotection protocol described herein is expected to be a useful addition to the presently available methods for performing the above transformation.

  DOI：

  10.1021/jo7021923

文献信息

• Trimethylsilyl Trifluoromethanesulfonate (TMSOTf) Assisted Facile Deprotection of <i>N</i>,<i>O</i>-Acetonides
  作者：Kevin W. C. Poon、Kimberly M. Lovell、Kendra N. Dresner、Apurba Datta

  DOI：10.1021/jo7021923

  日期：2008.1.1

  [GRAPHICS]Employing TMSOTf as an easily available reagent, we have developed a mild and efficient method for the deprotection of both terminal and internal NO-acetonide functionalities. Various regularly used protecting groups and common organic functional moieties were found to be unaffected by the described reaction conditions. In a few representative examples, the present method was also extended to deprotect acetonides obtained from 1,2-, and 1,3-terminal diols. The acetonide deprotection protocol described herein is expected to be a useful addition to the presently available methods for performing the above transformation.