3,5-O-[2-((S)-oxiranyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose | 337903-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-O-[2-((S)-oxiranyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: (1S,2R,6R,8R,11S)-4,4-dimethyl-11-[2-[(2S)-oxiran-2-yl]phenyl]-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane
• CAS: 337903-23-8
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: MFISLUACCOEWCN-VJQRDGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-O-[2-((S)-oxiranyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (3S)-3-benzyloxymethyl-1,3-dihydro-1-methoxybenzo[c]furan
  参考文献：
  名称：

  Facile separation of chiral 1,3-dihydrobenzo[ c ]furan derivatives using a d -xylose moiety as a protecting group

  摘要：

  1,2-O-Isopropylidene-alpha -D-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzo[c]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00488-2
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 3,5-O-[2-((S)-oxiranyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Facile separation of chiral 1,3-dihydrobenzo[ c ]furan derivatives using a d -xylose moiety as a protecting group

  摘要：

  1,2-O-Isopropylidene-alpha -D-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzo[c]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00488-2

文献信息

• Facile separation of chiral 1,3-dihydrobenzo[ c ]furan derivatives using a d -xylose moiety as a protecting group
  作者：David F. Ewing、Christophe Len、Grahame Mackenzie、Gino Ronco、Pierre Villa

  DOI：10.1016/s0957-4166(00)00488-2

  日期：2000.12

  1,2-O-Isopropylidene-alpha -D-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzo[c]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues. (C) 2001 Published by Elsevier Science Ltd.