methyl (R)-4,6-O-benzylidene-2-O-(2,2-dimethylpropanoyl)-α-D-ribohexopyranosid-3-ulose | 130130-72-2

• 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 (R)-4,6-O-benzylidene-2-O-(2,2-dimethylpropanoyl)-α-D-ribohexopyranosid-3-ulose
• 英文别名: Methyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-ribo-hexopyranosid-3-uloside
• CAS: 130130-72-2
• 化学式: C₁₉H₂₄O₇
• 分子量: 364.395
• InChiKey: LYTJYHOOKQCZEZ-NHMWIVBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (R)-4,6-O-benzylidene-2-O-(2,2-dimethylpropanoyl)-α-D-ribohexopyranosid-3-ulose 、 乙氧甲酰基亚甲基三苯基膦 以 乙腈 为溶剂， 反应 0.17h， 以63%的产率得到methyl (R)-4,6-O-benzylidene-2-O-(2,2-dimethylpropanoyl)-α-D-ribohexopyranosid-3-ulose
  参考文献：
  名称：

  Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins’ Bicyclic Sugar Moiety

  摘要：

  2-O-Acyl protected-d-ribo-3-uloses reacted with [(ethoxycarbonyl)methylene]triphenylphosphorane in acetonitrile to afford regio- and stereoselectively 2-(Z)-alkenes in 10-60 min under microwave irradiation. This domino reaction is proposed to proceed via tautomerization of 3-ulose to enol, acyl migration, tautomerization to the 3-O-acyl-2-ulose, and Wittig reaction. Alternatively, in chloroform, regioselective 3-olefination of 2-O-pivaloyl-3-uloses gave (E)-alkenes, key precursors for the miharamycins' bicyclic sugar moiety.

  DOI：

  10.1021/acs.orglett.5b02849
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside 在 重铬酸吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到methyl (R)-4,6-O-benzylidene-2-O-(2,2-dimethylpropanoyl)-α-D-ribohexopyranosid-3-ulose
  参考文献：
  名称：

  Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins’ Bicyclic Sugar Moiety

  摘要：

  2-O-Acyl protected-d-ribo-3-uloses reacted with [(ethoxycarbonyl)methylene]triphenylphosphorane in acetonitrile to afford regio- and stereoselectively 2-(Z)-alkenes in 10-60 min under microwave irradiation. This domino reaction is proposed to proceed via tautomerization of 3-ulose to enol, acyl migration, tautomerization to the 3-O-acyl-2-ulose, and Wittig reaction. Alternatively, in chloroform, regioselective 3-olefination of 2-O-pivaloyl-3-uloses gave (E)-alkenes, key precursors for the miharamycins' bicyclic sugar moiety.

  DOI：

  10.1021/acs.orglett.5b02849

文献信息

• Rashid, Abdul; Taylor, G. Mark; Wood, William W., Journal of the Chemical Society. Perkin transactions I, 1990, # 5, p. 1289 - 1296
  作者：Rashid, Abdul、Taylor, G. Mark、Wood, William W.、Alker, David

  DOI：——

  日期：——