[(2R)-2-[(2R,3S,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-oxooxolan-2-yl]-2-hydroxyethyl] (E)-3-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]prop-2-enoate | 1394245-90-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [(2R)-2-[(2R,3S,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-oxooxolan-2-yl]-2-hydroxyethyl] (E)-3-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]prop-2-enoate
• CAS: 1394245-90-9
• 化学式: C₃₉H₇₂O₉Si₄
• 分子量: 797.337
• InChiKey: JUTXOCAESBPENC-WFVRNUHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.08
• 重原子数：
  52
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R)-2-[(2R,3S,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-oxooxolan-2-yl]-2-hydroxyethyl] (E)-3-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]prop-2-enoate 在 三氟化硼乙醚 、 水 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以50%的产率得到trans-caffeoyl-6-O-D-glucono-γ-lactone
  参考文献：
  名称：

  First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata

  摘要：

  The first stereocontrolled synthesis of vittarilide-A and its C5-epimer was completed from D-glucuronolactone. Comparison with the spectroscopic properties reported for authentic material has given a clear indication as to the absolute stereochemistry of the natural vittarilide-A. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.105
• 作为产物：
  描述：

  TRANS-咖啡酸 在 咪唑 、 4-二甲氨基吡啶 、 水 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 [(2R)-2-[(2R,3S,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-oxooxolan-2-yl]-2-hydroxyethyl] (E)-3-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]prop-2-enoate
  参考文献：
  名称：

  First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata

  摘要：

  The first stereocontrolled synthesis of vittarilide-A and its C5-epimer was completed from D-glucuronolactone. Comparison with the spectroscopic properties reported for authentic material has given a clear indication as to the absolute stereochemistry of the natural vittarilide-A. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.105

文献信息

• First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata
  作者：Masaki Takahashi、Yusuke Murata、Yuki Hakamata、Kohei Suzuki、Tetsuya Sengoku、Hidemi Yoda

  DOI：10.1016/j.tet.2012.06.105

  日期：2012.9

  The first stereocontrolled synthesis of vittarilide-A and its C5-epimer was completed from D-glucuronolactone. Comparison with the spectroscopic properties reported for authentic material has given a clear indication as to the absolute stereochemistry of the natural vittarilide-A. (C) 2012 Elsevier Ltd. All rights reserved.