(2S,3S,4R,5R)-2,3,5,6-tetrakis(phenylmethoxy)hexane-1,4-diol | 195304-41-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4R,5R)-2,3,5,6-tetrakis(phenylmethoxy)hexane-1,4-diol
• CAS: 195304-41-7
• 化学式: C₃₄H₃₈O₆
• 分子量: 542.672
• InChiKey: SIYBVMWSIOMOPX-KRFMAMIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-2,3,5,6-tetrakis(phenylmethoxy)hexane-1,4-diol 在 咪唑 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 (2R,4R,5S)-6-[tert-butyl(dimethyl)silyl]oxy-1,2,4,5-tetrakis(phenylmethoxy)hexan-3-one
  参考文献：
  名称：

  结构简化的zaragozic酸（角鲨抑素）：立体选择性制备3,4-未取代的衍生物

  摘要：

  从D-葡萄糖开始，立体选择性地制备了结构简化的3，4-未取代的扎拉果酸衍生物。本方法涉及乙烯基格氏试剂的立体选择性添加，1,2-二醇的选择性裂解以及C-6处羟基的区域选择性酰化。

  DOI：

  10.1016/s0040-4039(97)10407-5
• 作为产物：
  描述：

  methyl 2,3,5,6-tetra-O-benzylglucofuranoside 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 12.5h， 生成 (2S,3S,4R,5R)-2,3,5,6-tetrakis(phenylmethoxy)hexane-1,4-diol
  参考文献：
  名称：

  结构简化的zaragozic酸（角鲨抑素）：立体选择性制备3,4-未取代的衍生物

  摘要：

  从D-葡萄糖开始，立体选择性地制备了结构简化的3，4-未取代的扎拉果酸衍生物。本方法涉及乙烯基格氏试剂的立体选择性添加，1,2-二醇的选择性裂解以及C-6处羟基的区域选择性酰化。

  DOI：

  10.1016/s0040-4039(97)10407-5

文献信息

• Synthesis of novel ammonium and selenonium ions and their evaluation as inhibitors of UDP-galactopyranose mutase
  作者：Natacha Veerapen、Yue Yuan、David A.R. Sanders、B. Mario Pinto

  DOI：10.1016/j.carres.2004.07.012

  日期：2004.9

  The syntheses of two ammonium salts of 1,4-dideoxy-1,4-imino-D-galactitol containing erythritol sulfate side chains are described. The parent compound is a known inhibitor of the enzyme UDP-galactopyranose mutase (UDP-galactopyranose furanomutase, E.C. 5.4.99.9), which is responsible for the conversion of UDP-galactopyranose into UDP-galactofuranose and is presumably protonated in its active form. The side chain was chosen because it is present in a known sulfonium ion alpha-glucosidase inhibitor, salacinol. The syntheses of the selenonium analogues derived from 1,4-dideoxy-1,4-seleno-D-galactitol are also described. The synthetic strategy in the syntheses of all four salts involved the nucleophilic attack of a protected derivative of the alditol at the least hindered carbon of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate to give adducts that were subsequently deprotected. The importance of different protecting groups used in the various syntheses is also highlighted. Enzyme inhibition assays carried out on these compounds, and the corresponding sulfonium ions synthesized previously, show that they are poor inhibitors of UDP-galactopyranose mutase. (C) 2004 Elsevier Ltd. All rights reserved.