5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol | 605668-77-7

• 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: 5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol
• 英文别名: (2R,3R,4S)-4-bromo-1-[(S)-(4-methylphenyl)sulfinyl]-5-phenylmethoxypentane-2,3-diol
• CAS: 605668-77-7
• 化学式: C₁₉H₂₃BrO₄S
• 分子量: 427.359
• InChiKey: DJCRUFBJQAGXTM-NUDCOPPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  86
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol 在 sodium azide 、 camphor-10-sulfonic acid 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 10.0h， 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：

  Novel, efficient and stereospecific synthesis of xylo-(2R,3S,4S)-phytosphingosine and threo-(2R,3R)-sphingosine

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(03)00427-0
• 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) 、 水 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以88%的产率得到5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol
  参考文献：
  名称：

  Novel, efficient and stereospecific synthesis of xylo-(2R,3S,4S)-phytosphingosine and threo-(2R,3R)-sphingosine

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(03)00427-0

文献信息

• Stereoselective total synthesis of (+)-aspicilin
  作者：Sadagopan Raghavan、T. Sreekanth

  DOI：10.1016/j.tetlet.2006.05.043

  日期：2006.7

  A stereoselective synthesis of (+)-aspicilin is described. Regio- and stereoselective functionalization by intramolecular participation of the sulfinyl group, ene reaction, and macrolactonization by Wadsworth–Emmons reaction employing Masamune–Roush protocol are the key steps of the route.

  描述了（+）-aspicilin的立体选择性合成。分子内参与亚磺酰基的区域和立体选择性功能化，烯键反应以及采用Masamune-Roush方案通过Wadsworth-Emmons反应进行大内酰胺化是该路线的关键步骤。
• 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.