n-octyl 4,6-O-benzylidene-α-D-glucopyranoside | 695228-29-6

• 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: n-octyl 4,6-O-benzylidene-α-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8R,8aS)-6-octoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 695228-29-6
• 化学式: C₂₁H₃₂O₆
• 分子量: 380.481
• InChiKey: CBYZDFQCAFRHGO-YVYPMRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  n-octyl 4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 molecular sieve 、 碘甲烷 作用下， 以 二氯甲烷 为溶剂， 反应 78.0h， 生成 n-octyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Directing Effect of Axial and Equatorial Anomeric Substituent in Site Specific Glycosylation of Glucopyranosides

  摘要：

  Regio- and stereoselective glycosylation of alpha- and beta-octyl glucopyranoside derivatives 2c and 2d, respectively, with glycosyl donor 3 to obtain the corresponding 3-O-linked 5c and 2-O-linked 4d saccharides, respectively, is described, formation of diglycosylated products 6c and 6d was not observed.

  DOI：

  10.1081/scc-120028637
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 辛基-D-吡喃葡萄糖苷 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以20%的产率得到n-octyl 4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and evaluation of antimigratory and antiproliferative activities of lipid-linked [13]-macro-dilactones

  摘要：

  The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound 13 was the most potent in the series, while compound 10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl alpha-glucoside 4,6-diol. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.083

文献信息

• Directing Effect of Axial and Equatorial Anomeric Substituent in Site Specific Glycosylation of Glucopyranosides
  作者：Hari Babu Mereyala、S. Bhavani、A. P. Rudradas

  DOI：10.1081/scc-120028637

  日期：2004.12.31

  Regio- and stereoselective glycosylation of alpha- and beta-octyl glucopyranoside derivatives 2c and 2d, respectively, with glycosyl donor 3 to obtain the corresponding 3-O-linked 5c and 2-O-linked 4d saccharides, respectively, is described, formation of diglycosylated products 6c and 6d was not observed.
• Synthesis and evaluation of antimigratory and antiproliferative activities of lipid-linked [13]-macro-dilactones
  作者：Anniefer N. Magpusao、Richard T. Desmond、Katelyn J. Billings、Gabriel Fenteany、Mark W. Peczuh

  DOI：10.1016/j.bmcl.2010.07.083

  日期：2010.9

  The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound 13 was the most potent in the series, while compound 10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl alpha-glucoside 4,6-diol. (c) 2010 Elsevier Ltd. All rights reserved.