(2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran, α-isomer | 1054605-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran, α-isomer
• 英文别名: (2R,3S,6S)-6-methoxy-3-phenylmethoxy-2-(phenylmethoxymethyl)oxane
• CAS: 1054605-91-2
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: ARBQFTAOTBQPPE-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran, α-isomer 、 2-(三甲基硅氧基)丙烯 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 1-[(2S,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]propan-2-one 、 1-[(2R,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]propan-2-one
  参考文献：
  名称：

  Diastereoselective Synthesis of 2′,3′-Dideoxy- β-C- Glucopyranosides as Intermediates for the Synthesis of 2′,3′-Dideoxy-β-D-Glucopyranosyl-C-Nucleosides

  摘要：

  An extension of the Vorbruggen method of nucleotide synthesis for the synthesis of G glucopyranosides, as intermediates for C-nucleosides, is described. It could be shown that the diastereoselectivity of the reaction can be tuned by a simple change of protecting groups.

  DOI：

  10.1080/15257770701508695
• 作为产物：
  描述：

  methyl 2,3-dideoxy-α-D-erythro-hexopyranoside 、 溴甲苯 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran, α-isomer
  参考文献：
  名称：

  Diastereoselective Synthesis of 2′,3′-Dideoxy- β-C- Glucopyranosides as Intermediates for the Synthesis of 2′,3′-Dideoxy-β-D-Glucopyranosyl-C-Nucleosides

  摘要：

  An extension of the Vorbruggen method of nucleotide synthesis for the synthesis of G glucopyranosides, as intermediates for C-nucleosides, is described. It could be shown that the diastereoselectivity of the reaction can be tuned by a simple change of protecting groups.

  DOI：

  10.1080/15257770701508695

文献信息

• Diastereoselective Synthesis of 2′,3′-Dideoxy- β-<i>C</i>- Glucopyranosides as Intermediates for the Synthesis of 2′,3′-Dideoxy-β-D-Glucopyranosyl-<i>C</i>-Nucleosides
  作者：Michael Löpfe、Jay S. Siegel

  DOI：10.1080/15257770701508695

  日期：2007.11.26

  An extension of the Vorbruggen method of nucleotide synthesis for the synthesis of G glucopyranosides, as intermediates for C-nucleosides, is described. It could be shown that the diastereoselectivity of the reaction can be tuned by a simple change of protecting groups.