(S)-2-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-oxirane | 612050-87-0

• 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: (S)-2-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-oxirane
• 英文别名: (2S)-2-[(1S)-1-[(4-methoxyphenyl)methoxy]-3-phenylmethoxypropyl]oxirane
• CAS: 612050-87-0
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: GVBMINSVDNWCFC-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-oxirane 在 sodium periodate 、 magnesium bromide diethyl etherate 、 水 、 四丁基碘化铵 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  Spirastrellolide B: Construction of the C(26)–C(40) Northern Hemisphere and a Related [5,5,7]-Bis-spiroketal Analogue

  摘要：

  Differential synthetic access to an advanced C26-C40 northern hemisphere fragment of splrastrellolide B and to a related [5,5,7]-bis-spiroketal analogue from a common intermediate has been achieved. Central to this venture is the regiocontrolled functionalization of a C(31-32) alkyne, exploiting different transition metal catalysts (cf. Pt-II and Au-I).

  DOI：

  10.1021/ol301795a
• 作为产物：
  描述：

  4-甲氧基氯苄 、 (S)-3-Benzyloxy-1-(S)-oxiranyl-propan-1-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以88%的产率得到(S)-2-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-oxirane
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin

  摘要：

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01667-8

文献信息

• Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin
  作者：Hyunjoo Lee、Hyoungsu Kim、Seungyoup Baek、Sanghee Kim、Deukjoon Kim

  DOI：10.1016/s0040-4039(03)01667-8

  日期：2003.8

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.
• Spirastrellolide B: Construction of the C(26)–C(40) Northern Hemisphere and a Related [5,5,7]-Bis-spiroketal Analogue
  作者：Xiaozhao Wang、Thomas J. Paxton、Ningkun Li、Amos B. Smith

  DOI：10.1021/ol301795a

  日期：2012.8.3

  Differential synthetic access to an advanced C26-C40 northern hemisphere fragment of splrastrellolide B and to a related [5,5,7]-bis-spiroketal analogue from a common intermediate has been achieved. Central to this venture is the regiocontrolled functionalization of a C(31-32) alkyne, exploiting different transition metal catalysts (cf. Pt-II and Au-I).