methyl 4,6-O-(R)-benzylidene-2-O-ethyl-α-D-arabinohexopyranosid-3-ulose | 1333398-05-2

• 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 4,6-O-(R)-benzylidene-2-O-ethyl-α-D-arabinohexopyranosid-3-ulose
• 英文别名: (2R,4aR,6S,7R,8aR)-7-ethoxy-6-methoxy-2-phenyl-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-8-one
• CAS: 1333398-05-2
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: QPJKEASUEJONCT-JZYAIQKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 在 四丁基硫酸氢铵 、 pyridinium chlorochromate 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 4,6-O-(R)-benzylidene-2-O-ethyl-α-D-arabinohexopyranosid-3-ulose
  参考文献：
  名称：

  New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

  摘要：

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.014
• 作为试剂：
  描述：

  三苯乙烯 在 Oxone 、 methyl 4,6-O-(R)-benzylidene-2-O-ethyl-α-D-arabinohexopyranosid-3-ulose 、 四丁基硫酸氢铵 、 edetate disodium 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 (S)-2,2,3-triphenyloxirane 、 噁丙环,三苯基-,(3R)-
  参考文献：
  名称：

  New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

  摘要：

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.014

文献信息

• New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars
  作者：José M. Vega-Pérez、Ignacio Periñán、Margarita Vega-Holm、Carlos Palo-Nieto、Fernando Iglesias-Guerra

  DOI：10.1016/j.tet.2011.07.014

  日期：2011.9

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.