methyl-4,6-O-(naphthyl-2'-methylidene)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl-4,6-O-(naphthyl-2'-methylidene)-α-D-glucopyranoside
• 英文别名: α-MeNGH2；(4aR,6S,7R,8R,8aS)-6-methoxy-2-naphthalen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• 化学式: C₁₈H₂₀O₆
• 分子量: 332.353
• InChiKey: YJIFFOONNJBFSB-LPETVPRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  methyl-4,6-O-(naphthyl-2'-methylidene)-α-D-glucopyranoside 、 异丁酸酐 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以76%的产率得到methyl 4,6-O-(2-naphthalenylidene)-3-O-isobutyryl-α-D-glucopyranoside
  参考文献：
  名称：

  Site-Selective Acylation of Carbohydrates Directed by Recyclable Polymer-Supported Isothiourea Catalysts

  摘要：

  The polystyrene-supported isothiourea catalysts, derived from the homogeneous catalyst BTMs, were synthesized and applied to the site-selective acylation of carbohydrates. The catalysts can be recovered and reused conveniently for 10 cycles without significantly loss in either activity or selectivity. It offers a sustainable and environmentally benign approach for the site-selective functionalization of carbohydrates.

  DOI：

  10.3987/com-18-14025

文献信息

• Structural Consequences in α‐ and β‐Glucopyranosidato Complexes of Cp*TiCl ₃
  作者：Dirk Schwidom、Daniela Zeysing、Michael Schmidt、Jürgen Heck

  DOI：10.1002/ejic.200900753

  日期：2009.12

  AbstractThe reaction of methyl‐4,6‐O‐(naphthyl‐2′‐methylidene)‐α‐D‐glucopyranoside (α‐MeNGH2) with trichloridopentamethylcyclopentadienyltitanium [Cp*TiCl3] and triethylamine in toluene reveals the dinuclear complex [(Cp*TiCl)‐μ‐(α‐MeNG)]2 (2). Complex 2 was characterized by elemental analysis, 1H and 13C NMR spectroscopy, circular dichroism, as well as single‐crystal structure analysis. Compared to the complex with the β‐anomer of the ligand in [(Cp*TiCl)‐μ‐(β‐MeNG)]2 (1), it is obvious that the absolute configuration of the Ti atoms in 2 have changed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)