(1'R)-p-methoxyphenyl 6-deoxy-2,3-O-(1-naphthyl)ethylidene-α-L-rhamnopyranoside | 1012786-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'R)-p-methoxyphenyl 6-deoxy-2,3-O-(1-naphthyl)ethylidene-α-L-rhamnopyranoside
• 英文别名: (2R,3aR,4S,6S,7S,7aR)-4-(4-methoxyphenoxy)-2,6-dimethyl-2-naphthalen-1-yl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 1012786-50-3
• 化学式: C₂₅H₂₆O₆
• 分子量: 422.478
• InChiKey: SYLDIOGXLOMVLE-DLIJGAEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1'R)-p-methoxyphenyl 6-deoxy-2,3-O-(1-naphthyl)ethylidene-α-L-rhamnopyranoside 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以93%的产率得到(1'R)-p-methoxyphenyl 4-O-acetyl-6-deoxy-2,3-O-(1-naphthyl)ethylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and chiroptical properties of (naphthyl)ethylidene ketals of carbohydrates in solution and solid state

  摘要：

  1,3-Dioxolane- and dioxane-type (1- and 2-naphthyl)ethylidene ketals of p-methoxyphenyl alpha-L-rhamnopyranoside and beta-D-glucopyranoside were prepared and their stereochemistry studied by solution and solid-state circular dichroism, X-ray diffraction, and coupled-oscillator CD calculations on the solid-state and MMFF-calculated geometries. Intermolecular exciton-coupled interactions between the nearby aromatic chromophores in the solid state and different conformers in solution and solid state could be identified as the main reason for the difference between solution and solid-state CDs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.011
• 作为产物：
  描述：

  4-methoxyphenyl α-L-rhamnopyranoside 、 1-Acetonaphthone dimethyl acetal 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以89%的产率得到(1'R)-p-methoxyphenyl 6-deoxy-2,3-O-(1-naphthyl)ethylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and chiroptical properties of (naphthyl)ethylidene ketals of carbohydrates in solution and solid state

  摘要：

  1,3-Dioxolane- and dioxane-type (1- and 2-naphthyl)ethylidene ketals of p-methoxyphenyl alpha-L-rhamnopyranoside and beta-D-glucopyranoside were prepared and their stereochemistry studied by solution and solid-state circular dichroism, X-ray diffraction, and coupled-oscillator CD calculations on the solid-state and MMFF-calculated geometries. Intermolecular exciton-coupled interactions between the nearby aromatic chromophores in the solid state and different conformers in solution and solid state could be identified as the main reason for the difference between solution and solid-state CDs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.011

文献信息

• Synthesis and chiroptical properties of (naphthyl)ethylidene ketals of carbohydrates in solution and solid state
  作者：Gábor Kerti、Tibor Kurtán、Anikó Borbás、Zoltán B. Szabó、András Lipták、László Szilágyi、Zita Illyés-Tünde、Attila Bényei、Sándor Antus、Masayuki Watanabe、Ettore Castiglioni、Gennaro Pescitelli、Piero Salvadori

  DOI：10.1016/j.tet.2007.12.011

  日期：2008.2

  1,3-Dioxolane- and dioxane-type (1- and 2-naphthyl)ethylidene ketals of p-methoxyphenyl alpha-L-rhamnopyranoside and beta-D-glucopyranoside were prepared and their stereochemistry studied by solution and solid-state circular dichroism, X-ray diffraction, and coupled-oscillator CD calculations on the solid-state and MMFF-calculated geometries. Intermolecular exciton-coupled interactions between the nearby aromatic chromophores in the solid state and different conformers in solution and solid state could be identified as the main reason for the difference between solution and solid-state CDs. (C) 2007 Elsevier Ltd. All rights reserved.