4-[1-azido-2-benzyloxy-(1R)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane | 605668-79-9

• 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: 4-[1-azido-2-benzyloxy-(1R)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane
• 英文别名: (4S,5R)-4-[(1R)-1-azido-2-phenylmethoxyethyl]-2,2-dimethyl-5-[[(S)-(4-methylphenyl)sulfinyl]methyl]-1,3-dioxolane
• CAS: 605668-79-9
• 化学式: C₂₂H₂₇N₃O₄S
• 分子量: 429.54
• InChiKey: IGYLYQRZZLVQLY-LIASHVPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[1-azido-2-benzyloxy-(1R)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane 在 三乙胺 、 三氟乙酸酐 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以73%的产率得到[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol
  参考文献：
  名称：

  The sulfinyl moiety as an internal nucleophile. Part 8: Efficient, stereospecific synthesis of (+)-polyoxamic acid

  摘要：

  A straightforward and stereospecific synthesis of (+)-polyoxamic acid is disclosed. The key step of the synthesis involves the regio- and stereospecific bromohydration of an olefin via intramolecular participation by the sulfinyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01650-2
• 作为产物：
  描述：

  5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 camphor-10-sulfonic acid 、 水 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 7.25h， 生成 4-[1-azido-2-benzyloxy-(1R)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane
  参考文献：
  名称：

  The sulfinyl moiety as an internal nucleophile. Part 8: Efficient, stereospecific synthesis of (+)-polyoxamic acid

  摘要：

  A straightforward and stereospecific synthesis of (+)-polyoxamic acid is disclosed. The key step of the synthesis involves the regio- and stereospecific bromohydration of an olefin via intramolecular participation by the sulfinyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01650-2

文献信息

• Novel, efficient and stereospecific synthesis of xylo-(2R,3S,4S)-phytosphingosine and threo-(2R,3R)-sphingosine
  作者：Sadagopan Raghavan、A. Rajender、J.S. Yadav

  DOI：10.1016/s0957-4166(03)00427-0

  日期：2003.7

  The stereo- and regioselective elaboration of a bromohydrin from an olefinic precursor and Pummerer ene reaction for carbon-carbon bond formation are the key steps in a novel and flexible synthesis of xylo-phytosphingosine and threo-sphingosine. (C) 2003 Elsevier Ltd. All rights reserved.
• The sulfinyl moiety as an internal nucleophile. Part 8: Efficient, stereospecific synthesis of (+)-polyoxamic acid
  作者：Sadagopan Raghavan、Suju C. Joseph

  DOI：10.1016/s0040-4039(03)01650-2

  日期：2003.8

  A straightforward and stereospecific synthesis of (+)-polyoxamic acid is disclosed. The key step of the synthesis involves the regio- and stereospecific bromohydration of an olefin via intramolecular participation by the sulfinyl group. (C) 2003 Elsevier Ltd. All rights reserved.