(2R,6S)-2-((benzyloxy)methyl)-6-(octyloxy)-2H-pyran-3(6H)-one | 1427201-63-5

• 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,6S)-2-((benzyloxy)methyl)-6-(octyloxy)-2H-pyran-3(6H)-one
• 英文别名: (2S,6R)-2-octoxy-6-(phenylmethoxymethyl)-2H-pyran-5-one
• CAS: 1427201-63-5
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: CEZPJZOAOUJPPO-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,6S)-2-((benzyloxy)methyl)-6-(octyloxy)-2H-pyran-3(6H)-one 在 2,4,6-三甲基吡啶 、 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四氧化锇 、 水合氯化铈 、 N-甲基吗啉氧化物 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 1.5h， 生成 octyl 6-O-benzyl-4-O-triphenylmethyl-α-D-mannopyranosyl-(1→4)-6-O-benzyl-α-D-mannopyranoside
  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：

  (R)-1-(2-furyl)-2-O-benzyl-1,2-ethanediol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 Na⁽¹⁺⁾*CHO₃^(1-)*3H₂O 、 sodium acetate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (2R,6S)-2-((benzyloxy)methyl)-6-(octyloxy)-2H-pyran-3(6H)-one
  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.