ethyl 3,4,6-tri-O-benzyl-2-C-phenyl-α-D-glucopyranoside | 1365092-32-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-benzyl-2-C-phenyl-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-ethoxy-3-phenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 1365092-32-5
• 化学式: C₃₅H₃₈O₆
• 分子量: 554.683
• InChiKey: BQNJBBGXIWZNHC-HPRFQDQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-iodo-3,4-dihydro-2H-pyran 在 disodium hydrogenphosphate 、 Oxone 、 Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 21.58h， 生成 ethyl 3,4,6-tri-O-benzyl-2-C-phenyl-α-D-glucopyranoside
  参考文献：
  名称：

  Phosphine-Free Suzuki–Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides

  摘要：

  A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-alpha-glycosides and 1,5-anhydro-2-C-ary1-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.

  DOI：

  10.1021/ol3003139

文献信息

• Phosphine-Free Suzuki–Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-<i>C</i>-Aryl-Glycosides
  作者：Isidro Cobo、M. Isabel Matheu、Sergio Castillón、Omar Boutureira、Benjamin G. Davis

  DOI：10.1021/ol3003139

  日期：2012.4.6

  A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-alpha-glycosides and 1,5-anhydro-2-C-ary1-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.