tert-butyl N-[(2S,3R)-1-[2-bromoethoxy(methoxy)phosphoryl]oxy-3-hydroxyoctadec-4-en-2-yl]carbamate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: tert-butyl N-[(2S,3R)-1-[2-bromoethoxy(methoxy)phosphoryl]oxy-3-hydroxyoctadec-4-en-2-yl]carbamate
• 化学式: C₂₆H₅₁BrNO₇P
• 分子量: 600.571
• InChiKey: IYRNDWNORPDWNQ-HAIUTTLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  36
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S,3R)-1-[2-bromoethoxy(methoxy)phosphoryl]oxy-3-hydroxyoctadec-4-en-2-yl]carbamate 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

  摘要：

  Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state H-2 NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (L-o) domains in the raft-mimicking mixed bilayers. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.014
• 作为产物：
  描述：

  N-甲氧基-N-甲基-N2-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酰胺 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 4-二甲氨基吡啶 、 四溴化碳 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.67h， 生成 tert-butyl N-[(2S,3R)-1-[2-bromoethoxy(methoxy)phosphoryl]oxy-3-hydroxyoctadec-4-en-2-yl]carbamate
  参考文献：
  名称：

  Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

  摘要：

  Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state H-2 NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (L-o) domains in the raft-mimicking mixed bilayers. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.014

文献信息

• Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior
  作者：Jin Cui、Shigeru Matsuoka、Masanao Kinoshita、Nobuaki Matsumori、Fuminori Sato、Michio Murata、Jun Ando、Hiroyuki Yamakoshi、Kosuke Dodo、Mikiko Sodeoka

  DOI：10.1016/j.bmc.2015.05.014

  日期：2015.7

  Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state H-2 NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (L-o) domains in the raft-mimicking mixed bilayers. (C) 2015 Elsevier Ltd. All rights reserved.