(2R)-2-[(4-methoxyphenyl)methoxy]hexadecanal | 1233218-77-3

• 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: (2R)-2-[(4-methoxyphenyl)methoxy]hexadecanal
• CAS: 1233218-77-3
• 化学式: C₂₄H₄₀O₃
• 分子量: 376.58
• InChiKey: CHZYNUWYBFGBIE-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(4-methoxyphenyl)methoxy]hexadecanal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 1-deoxy-1-[(4'R,2'E)-4'-(4''-methoxybenzyloxy)-2'-octadecenyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose
  参考文献：
  名称：

  Total Synthesis of α-1C-Galactosylceramide, an Immunostimulatory C-Glycosphingolipid, and Confirmation of the Stereochemistry in the First-Generation Synthesis

  摘要：

  A nonisosteric alpha-C-glycoside analogue of KRN7000 (alpha-1C-GalCer, 1) was reported to induce a selective type of cytokine release in human invariant natural killer cells in vitro. We report here a very concise synthetic route to 1 and its analogue 1'. The key steps include olefin cross-metathesis, Sharpless asymmetric epoxidation, and epoxide opening by NaN3/NH4Cl. Inversion of configuration at the amide-bearing carbon in the phytosphingosine backbone constructed by epoxide opening in our previous synthesis of 1 was verified, indicating that remote group participation is not involved during the epoxide-opening reaction.

  DOI：

  10.1021/jo201450s
• 作为产物：
  描述：

  (2R)-2-[(4-methoxyphenyl)methoxy]hexadecan-1-ol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 水 、 碳酸氢钠 、 sodium bromide 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 1.17h， 以62%的产率得到(2R)-2-[(4-methoxyphenyl)methoxy]hexadecanal
  参考文献：
  名称：

  Synthesis of Immunostimulatory α-C-Galactosylceramide Glycolipids via Sonogashira Coupling, Asymmetric Epoxidation, and Trichloroacetimidate-Mediated Epoxide Opening

  摘要：

  Stereocontrolled syntheses of alpha-C-GalCer (2) and its alpha-C-acetylenic analogue 6 were accomplished in high efficiency by a convergent construction strategy from 1-hexadecene and D-galactose. The key transformations include Sonogashira coupling, Sharpless asymmetric epoxidation, and Et(2)AlCl-catalyzed cyclization of an epoxytrichloroacetimidate to generate protected dihydrooxazine 21.

  DOI：

  10.1021/ol1009976

文献信息

• The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000
  作者：Ahmad S. Altiti、Stewart Bachan、David R. Mootoo

  DOI：10.1021/acs.orglett.6b02284

  日期：2016.9.16

  A synthesis of glycosphingolipids that centers on the reaction of O- and C-glycosyl crotylstannanes and relatively simple lipid aldehydes is described. The modularity of this strategy and versatility of the crotylation products make this an attractive approach to diverse, highly substituted libraries. The methodology is applied to analogues of the potent imunostimulatory glycolipid KRN7000, including

  描述了以O-和C-糖基巴豆基stananes与相对简单的脂质醛的反应为中心的鞘糖脂的合成。这种策略的模块化和crotylation产品的多功能性，使其成为吸引各种高度替代图书馆的有吸引力的方法。该方法学适用于强效免疫刺激性糖脂KRN7000的类似物，包括带有非对映神经酰胺片段和2-酰胺基取代基的O-，亚甲基和氟亚甲基连接的等排体。