3-O-Octyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside | 103526-80-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-Octyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside
• 英文别名: 1,2:5,6-Di-O-isopropylidene-3-O-octyl-α-D-glucofuranose；3-O-octyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-octoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 103526-80-3
• 化学式: C₂₀H₃₆O₆
• 分子量: 372.502
• InChiKey: XOLWPGKWBGYUNQ-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-O-Octyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside 在 吡啶 、 氢氧化钾 、 sodium hydroxide 、 硫酸 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 73.0h， 生成 6-O-(3-Deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-1,2-O-isopropylidene-3-O-octyl-α-D-glucofuranose
  参考文献：
  名称：

  Goueth, Pierre Y.; Ronco, Gino; Villa, Pierre, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 679 - 696

  摘要：

  DOI：
• 作为产物：
  描述：

  双丙酮葡萄糖 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 生成 3-O-Octyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside
  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

• Lipophilic sugar nucleotide synthesis by structure-based design of nucleotidylyltransferase substrates
  作者：Malcolm P. Huestis、Gaia A. Aish、Joseph P. M. Hui、Evelyn C. Soo、David L. Jakeman

  DOI：10.1039/b716955h

  日期：——

  Structure-based design of alkyl sugar-1-phosphates provides an efficient nucleotidylyltransferase-catalyzed synthesis of a series of new lipophilic sugar nucleotides possessing long or branched alkyl chains, thereby demonstrating the utility of nucleotidylyltransferases to catalyze the synthesis of sugar nucleotides with potential applications in lipopolysaccharide and lipoglycopeptide biosynthesis.

  基于结构的烷基糖-1-磷酸酯设计提供了一种高效的核苷酸转移酶催化合成一系列新型脂溶性糖核苷酸的方法，这些糖核苷酸具有较长或支链的烷基链，从而展示了核苷酸转移酶在催化合成具有潜在应用于脂多糖和脂糖肽生物合成的糖核苷酸方面的实用性。
• Urata, Kouichi; Yano, Shinji; Takaishi, Naotake, Journal of the American Oil Chemists' Society, 1995, vol. 72, # 1, p. 73 - 82
  作者：Urata, Kouichi、Yano, Shinji、Takaishi, Naotake

  DOI：——

  日期：——
• Structure–Activity Relationships for Antibacterial to Antifungal Conversion of Kanamycin to Amphiphilic Analogues
  作者：Marina Fosso、Madher N. AlFindee、Qian Zhang、Vincent de Paul Nzuwah Nziko、Yukie Kawasaki、Sanjib K. Shrestha、Jeremiah Bearss、Rylee Gregory、Jon Y. Takemoto、Cheng-Wei Tom Chang

  DOI：10.1021/acs.joc.5b00248

  日期：2015.5.1

  Novel fungicides are urgently needed. It was recently reported that the attachment of an octyl group at the O-4 '' position of kanamycin B converts this antibacterial aminoglycoside into a novel antifungal agent. To elucidate the structure-activity relationship (SAR) for this phenomenon, a lead compound FG03 with a hydroxyl group replacing the 3 ''-NH2 group of kanamycin B was synthesized. FG03's antifungal activity and Synthetic scheme inspired the synthesis of a library of kanamycin B analogues alkylated at various hydroxyl groups. SAR. studies of the library revealed that for antifungal activity the O-4 '' position is the optimal site for attaching a linear alkyl chain and that the 3 ''-NH2 and 6 ''-OH groups of the kanamycin B parent molecule are not essential for antifungal activity. The discovery of lead compound, FG03, is an example of reviving clinically obsolete drugs like kanamycin by simple chemical modification and an alternative strategy for discovering novel antimicrobials.
• 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：——
• Goueth, Pierre Y.; Gogalis, Pascalis; Bikanga, Raphael, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 2, p. 249 - 272
  作者：Goueth, Pierre Y.、Gogalis, Pascalis、Bikanga, Raphael、Gode, Paul、Postel, Denis、et al.

  DOI：——

  日期：——