methyl 2-O-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside | 214068-00-5

• 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 2-O-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aS)-6-methoxy-2-(4-methoxyphenyl)-7-[(4-methoxyphenyl)methoxy]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 214068-00-5
• 化学式: C₂₃H₂₈O₈
• 分子量: 432.471
• InChiKey: CAGYVTFYFPOVRP-VGPVBAISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-O-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives

  摘要：

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.

  DOI：

  10.1021/jo980501r
• 作为产物：
  描述：

  methyl 4,6-O-p-methoxybenzylidene-α-D-glucopyranoside 、 4-甲氧基氯苄 在 四丁基碘化铵 、 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 以45%的产率得到methyl 2-O-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside
  参考文献：
  名称：

  Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives

  摘要：

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.

  DOI：

  10.1021/jo980501r

文献信息

• Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives
  作者：Jian Chen、Li Feng、Glenn D. Prestwich

  DOI：10.1021/jo980501r

  日期：1998.9.1

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.