3-O-myristyl-D-glucose | 91041-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-myristyl-D-glucose
• 英文别名: (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(tetradecyloxy)-tetrahydro-2H-pyran-2,3,5-triol；(3R,4S,5R,6R)-6-(hydroxymethyl)-4-tetradecoxyoxane-2,3,5-triol
• CAS: 91041-95-1
• 化学式: C₂₀H₄₀O₆
• 分子量: 376.534
• InChiKey: UHBINPARKZSORT-BNCGXOKJSA-N

物化性质

• 沸点：
  529.6±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-myristyl-D-glucose 在 氢氟酸 、 sodium acetate 作用下， 以 正己烷 为溶剂， 生成 Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-fluoro-4-tetradecyloxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Miethchen, Ralf; Holz, Jens; Peters, Dietmar, Zeitschrift fur Chemie, 1989, vol. 29, # 11, p. 420 - 421

  摘要：

  DOI：
• 作为产物：
  描述：

  双丙酮葡萄糖 在 Amberlite CG-120 (H⁺ type) 、 sodium hydride 作用下， 以 水 为溶剂， 反应 2.5h， 生成 3-O-myristyl-D-glucose
  参考文献：
  名称：

  Studies on synthesis of 3-O-alkyl-D-glucose and 3-O-alkyl-D-allose derivatives and their biological activities.

  摘要：

  合成了二十二种D-葡萄糖和D-阿洛糖的3-O-烷基衍生物、四种末端甲撑基的D-葡萄糖3-O-烯基衍生物和四种D-葡萄糖的3-O-ω-羟基烷基或-甲氧基烷基衍生物。测定了它们对体外培养的白血病L-5178Y细胞的细胞毒性、抗菌活性和植物生长抑制作用。

  DOI：

  10.1248/cpb.35.2894

文献信息

• Studies on synthesis of 3-O-alkyl-D-glucose and 3-O-alkyl-D-allose derivatives and their biological activities.
  作者：TETSURO IKEKAWA、KAZUHIKO IRINODA、KOICHI SAZE、TATSUHIKO KATORI、HIDEAKI MATSUDA、MASANORI OHKAWA、MARTIN KOSIK

  DOI：10.1248/cpb.35.2894

  日期：——

  Twenty two 3-Ο-alkyl derivatives of D-glucose and D-allose, four 3-Ο-alkenyl derivatives of D-glucose having an end methylene group, and four 3-Ο-ω-hydroxyalkyl- or -methoxyalkyl derivatives of D-glucose were synthesized. Their cytotoxicity in vitro against the cultured leukemia L-5178Y cell line, antimicrobial activity and plant growth-inhibitory effect were determined.

  合成了二十二种D-葡萄糖和D-阿洛糖的3-O-烷基衍生物、四种末端甲撑基的D-葡萄糖3-O-烯基衍生物和四种D-葡萄糖的3-O-ω-羟基烷基或-甲氧基烷基衍生物。测定了它们对体外培养的白血病L-5178Y细胞的细胞毒性、抗菌活性和植物生长抑制作用。
• Probing structure/affinity relationships for the Plasmodium falciparum hexose transporter with glucose derivatives
  作者：Martine Fayolle、Marina Ionita、Sanjeev Krishna、Christophe Morin、Asha Parbhu Patel

  DOI：10.1016/j.bmcl.2005.11.068

  日期：2006.3

  A series of 3-O-substituted glucose derivatives was prepared with alkyl, alkenyl, aromatic and ferrocenic substituents; to vary lipophilicity and hydrogen bonding ethylenedioxy and perfluorinated fragments were also introduced. Apparent affinities for the Plasmodium falciparum hexose transporter (PfHT) were determined after heterologous expression in Xenopus oocytes, with highest affinities for compounds with C8-C13 lipophilic chains. As no derivatives show significant affinity for the mammalian glucose transporter (GLUT1), these structure/affinity assays contribute to design of potent PfHT inhibitors and eventual development of antimalarials. (C) 2005 Elsevier Ltd. All rights reserved.
• Miethchen, Ralf; Holz, Jens; Peters, Dietmar, Zeitschrift fur Chemie, 1989, vol. 29, # 11, p. 420 - 421
  作者：Miethchen, Ralf、Holz, Jens、Peters, Dietmar

  DOI：——

  日期：——