(2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(octyloxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-ol | 1427201-94-2

• 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,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(octyloxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-ol
• 英文别名: (2R,3S,6S)-6-[[(2R,3S,6S)-6-[[(2R,3S,6S)-6-[[(2R,3S,6S)-6-octoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-3-yl]oxy]-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-3-yl]oxy]-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-3-yl]oxy]-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-3-ol
• CAS: 1427201-94-2
• 化学式: C₆₀H₇₄O₁₃
• 分子量: 1003.24
• InChiKey: GORJTWABAPHKGD-CRELNLGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  73
• 可旋转键数：
  30
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(octyloxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-ol 、 triphenylmethyl trifluoromethanesulfonate 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Regioselective Polymethylation of α-(1 → 4)-Linked Mannopyranose Oligosaccharides

  摘要：

  An approach has been developed of the regioselective methylation of alpha-(1 -> 4)-linked mannopyranose oligosaccharides via a four-step methodology. The key reaction involved n-Bu2SnCl2-mediated activation of cis-diols. By tuning protecting groups on the substrates, multiple cis-diols in the substrates were functionalized in a consistent and regioselective manner. Using optimized substrates and reaction conditions, regioselective methylation of di-, tri-, and tetrasaccharide substrates proceeded in isolated yields per cis-diol of 95, 88 and 79%, respectively. The methodology was also applied to functionalize trans-diols in alpha-cyclodextrin.

  DOI：

  10.1021/jo4001299
• 作为产物：
  描述：

  (2R,6R)-6-((benzyloxy)methyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl tert-butyl carbonate 在 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 水合氯化铈 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(((2R,3S,6S)-2-((benzyloxy)methyl)-6-(octyloxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-yl)oxy)-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Regioselective Polymethylation of α-(1 → 4)-Linked Mannopyranose Oligosaccharides

  摘要：

  An approach has been developed of the regioselective methylation of alpha-(1 -> 4)-linked mannopyranose oligosaccharides via a four-step methodology. The key reaction involved n-Bu2SnCl2-mediated activation of cis-diols. By tuning protecting groups on the substrates, multiple cis-diols in the substrates were functionalized in a consistent and regioselective manner. Using optimized substrates and reaction conditions, regioselective methylation of di-, tri-, and tetrasaccharide substrates proceeded in isolated yields per cis-diol of 95, 88 and 79%, respectively. The methodology was also applied to functionalize trans-diols in alpha-cyclodextrin.

  DOI：

  10.1021/jo4001299

文献信息

• Regioselective Polymethylation of α-(1 → 4)-Linked Mannopyranose Oligosaccharides
  作者：Li Xia、Todd L. Lowary

  DOI：10.1021/jo4001299

  日期：2013.4.5

  An approach has been developed of the regioselective methylation of alpha-(1 -> 4)-linked mannopyranose oligosaccharides via a four-step methodology. The key reaction involved n-Bu2SnCl2-mediated activation of cis-diols. By tuning protecting groups on the substrates, multiple cis-diols in the substrates were functionalized in a consistent and regioselective manner. Using optimized substrates and reaction conditions, regioselective methylation of di-, tri-, and tetrasaccharide substrates proceeded in isolated yields per cis-diol of 95, 88 and 79%, respectively. The methodology was also applied to functionalize trans-diols in alpha-cyclodextrin.