1-O-Hexadecyl-2-O-methyl-3-O-(4-methoxyphenyl)-sn-glycerol | 156737-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-O-Hexadecyl-2-O-methyl-3-O-(4-methoxyphenyl)-sn-glycerol
• 英文别名: 1-O-hexadecyl-2-O-methyl-3-O-(p-methoxyphenyl)-sn-glycerol；1-[(2R)-3-hexadecoxy-2-methoxypropoxy]-4-methoxybenzene
• CAS: 156737-66-5
• 化学式: C₂₇H₄₈O₄
• 分子量: 436.676
• InChiKey: QBCKVMASQOBUKU-HHHXNRCGSA-N

物化性质

• 沸点：
  521.1±40.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  31
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-O-Hexadecyl-2-O-methyl-3-O-(4-methoxyphenyl)-sn-glycerol 在 cerium nitrate 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氨 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.42h， 生成 (2R,3R,4R,5R,6R)-2-[(2R)-3-hexadecoxy-2-methoxypropoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
  参考文献：
  名称：

  Synthesis and Growth Inhibitory Properties of Glycosides of 1-O-Hexadecyl-2-O-methyl-sn-glycerol, Analogs of the Antitumor Ether Lipid ET-18-OCH₃ (Edelfosine)

  摘要：

  Glycosylated antitumor ether lipids (GAELs), analogs of 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine (1, ET-18-OCH3, edelfosine), were synthesized in good overall yields by glycosylation of 1-O-alkyl-2-O-methyl-sn-glycerol and tested for in vitro antineoplastic activity against a variety of murine and human tumor cell lines. Stereospecific glycosylation was achieved by the use of 2-O-acetyl-3,4,6-tri-O-benzylglucopyranosyl and -mannopyranosyl trichloroacetimidates as donors, with trimethylsilyl trifluoromethanesulfonate as catalyst in the presence of molecular sieves at -78 degrees C. The GAELs differ from 1 in having the sn-3-phosphocholine residue replaced by one of the following monosaccharide residues: beta- and alpha-2-deoxy-D-arabino-hexopyranosyl, alpha-D-mannopyranosyl, 2-O-methyl-beta-D-glucopyranosyl, and 2-O-methyl-alpha-D-mannopyranosyl. 1-O-Hexadecyl-2-O-methyl-3-O-(2'-deoxy-beta-D-arabino-hexopyranosyl)-sn-glycerol (2) was more effective than 1 in inhibiting the growth of MCF-7 (human breast cancer) and its adriamycin-resistant form MCF-7/adriamycin, and murine Lewis lung cancer. cells. 2-Deoxy-beta-D-arabino-hexopyranoside 2 was also an effective growth inhibitor of two drug-resistant leukemic cell lines, P388/Adr and L1210/vmdr.

  DOI：

  10.1021/jm960164j
• 作为产物：
  描述：

  1-O-hexadecyl-3-O-(p-methoxyphenyl)-sn-glycerol 以99%的产率得到
  参考文献：
  名称：

  Byun Hoe-Sup, Kumar Erukulla Ravi, Bittman Robert, J. Org. Chem, 59 (1994) N 9, S 2630- 2633

  摘要：

  DOI：

文献信息

• Modified ether glyceroglycolipids
  申请人：The Liposome Company, Inc.

  公开号：US06153736A1

  公开（公告）日：2000-11-28

  This invention provides lipids having: 1) a glycerol backbone; 2) a hydrocarbon chain, preferably saturated and containing 16 or 18 carbon atoms, attached to C-1 of the backbone by an ether linkage; 3) a methyl group attached to C-2 of the backbone, preferably by an ether linkage; and, 4) a sugar attached to C-3 of the glycerol backbone in either the alpha or beta anomeric configuration, the sugar being altered by modification of, or substitution for, one or more of its hydroxyl groups. Also provided herein are ether-lipid-containing compositions, as well as methods of administering such compositions to animals, for example, those afflicted with cancers, as well as various other diseases and disorders.

  本发明提供了具有以下特征的脂质：1）甘油骨架；2）连接到骨架C-1的烃链，优选为饱和的含有16或18个碳原子；3）连接到骨架C-2的甲基基团，优选为醚键连接；4）连接到甘油骨架C-3的糖，以α或β异构构型存在，该糖通过修饰或替换其一个或多个羟基而被改变。此外，本文还提供了含有醚脂质的组合物，以及将这些组合物用于动物，例如那些患有癌症以及其他各种疾病和障碍的动物的方法。
• Enantioselective Syntheses of 1-O-Benzyl-sn-glycerol and 1-O-Hexadecyl-2-O-methyl-sn-glycerol via Asymmetric Dihydroxylation of Allyl 4-Methoxyphenyl Ether. Use of AD-Mix Supplemented with Potassium Persulfate
  作者：Hoe-Sup Byun、Erukulla Ravi Kumar、Robert Bittman

  DOI：10.1021/jo00088a059

  日期：1994.5
• US6153736A
  申请人：——

  公开号：US6153736A

  公开（公告）日：2000-11-28
• US6573246B1
  申请人：——

  公开号：US6573246B1

  公开（公告）日：2003-06-03