1,2-di-O-oleoyl-3-O-[2',3',4',6'-tetra-O-(4''-methoxybenzyl)-β-D-glucopyranosyl]-sn-glycerol | 428862-90-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-di-O-oleoyl-3-O-[2',3',4',6'-tetra-O-(4''-methoxybenzyl)-β-D-glucopyranosyl]-sn-glycerol
• CAS: 428862-90-2
• 化学式: C₇₇H₁₁₄O₁₄
• 分子量: 1263.74
• InChiKey: XCIKJDQDZNMQCF-NZJCRQABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.27
• 重原子数：
  91.0
• 可旋转键数：
  53.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  144.9
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  1,2-di-O-oleoyl-3-O-[2',3',4',6'-tetra-O-(4''-methoxybenzyl)-β-D-glucopyranosyl]-sn-glycerol 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以58%的产率得到1,2-di-O-oleoyl-3-O-(β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and mesogenic properties of glycosyl diacylglycerols

  摘要：

  We synthesised glycosyl diacylglycerols bearing unsaturated or chiral methyl branched fatty acid chains. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method. The synthesised compounds displayed thermotropic S-A (lamellar), cubic and columnar phases and investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V-H phases, lamellar L-x phases and normal bicontinuous cubic V-I phases, The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00202-x
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 palladium on activated charcoal 甲醇 、 氢气 、 sodium methylate 、 氰化汞 、 sodium hydride 、 4-吡咯烷基吡啶 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 mercury dibromide 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 1,2-di-O-oleoyl-3-O-[2',3',4',6'-tetra-O-(4''-methoxybenzyl)-β-D-glucopyranosyl]-sn-glycerol
  参考文献：
  名称：

  Synthesis and mesogenic properties of glycosyl diacylglycerols

  摘要：

  We synthesised glycosyl diacylglycerols bearing unsaturated or chiral methyl branched fatty acid chains. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method. The synthesised compounds displayed thermotropic S-A (lamellar), cubic and columnar phases and investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V-H phases, lamellar L-x phases and normal bicontinuous cubic V-I phases, The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00202-x

文献信息

• RCM-Based Synthesis of a Variety of β-<i>C</i>-Glycosides and Their in Vitro Anti-Solid Tumor Activity
  作者：Maarten H. D. Postema、Jared L. Piper、Russell L. Betts、Frederick A. Valeriote、Halina Pietraszkewicz

  DOI：10.1021/jo040254t

  日期：2005.2.1

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.