[(2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-(phenylsulfanylmethyl)-4a,5,8,8a-tetrahydro-1,4-benzodioxin-5-yl]oxy-tert-butyl-dimethylsilane | 213536-10-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [(2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-(phenylsulfanylmethyl)-4a,5,8,8a-tetrahydro-1,4-benzodioxin-5-yl]oxy-tert-butyl-dimethylsilane
• CAS: 213536-10-8
• 化学式: C₂₅H₄₀O₅SSi
• 分子量: 480.741
• InChiKey: RGDMDYUFCLZDMN-BRPWVORNSA-N

物化性质

• 沸点：
  499.484±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.097±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-(phenylsulfanylmethyl)-4a,5,8,8a-tetrahydro-1,4-benzodioxin-5-yl]oxy-tert-butyl-dimethylsilane 在 2,6-二甲基吡啶 、 sodium chlorite 、 2-甲基-2-丁烯 、 间氯过氧苯甲酸 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 水 、 叔丁醇 为溶剂， 生成 莽草酸
  参考文献：
  名称：

  Direct conversion of 1,2-diol into allyl sulfide. Regioselective transformation of (−)-quinic acid to (−)-shikimic acid

  摘要：

  Exo-1,2-diols 3 and 4 were efficiently converted into the corresponding allyl sulfides by means of tri-n-butylphosphine (Bu3P) and diphenyl disulfide (PhS)(2). This method was applied to the introduction of a carbon-carbon double bond from diol 11 to give allyl sulfide 12 in a highly regioselective manner. The allyl sulfide 12 was transformed into (-)-shikimic acid (1) in four steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01239-8
• 作为产物：
  描述：

  (2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate 在 三丁基膦 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成 [(2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-(phenylsulfanylmethyl)-4a,5,8,8a-tetrahydro-1,4-benzodioxin-5-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Direct conversion of 1,2-diol into allyl sulfide. Regioselective transformation of (−)-quinic acid to (−)-shikimic acid

  摘要：

  Exo-1,2-diols 3 and 4 were efficiently converted into the corresponding allyl sulfides by means of tri-n-butylphosphine (Bu3P) and diphenyl disulfide (PhS)(2). This method was applied to the introduction of a carbon-carbon double bond from diol 11 to give allyl sulfide 12 in a highly regioselective manner. The allyl sulfide 12 was transformed into (-)-shikimic acid (1) in four steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01239-8

文献信息

• Ohtani, Yasuhiro; Shinada, Tetsuro; Ohfune, Yasufumi, Synlett, 2003, # 5, p. 619 - 622
  作者：Ohtani, Yasuhiro、Shinada, Tetsuro、Ohfune, Yasufumi

  DOI：——

  日期：——
• Direct conversion of 1,2-diol into allyl sulfide. Regioselective transformation of (−)-quinic acid to (−)-shikimic acid
  作者：Tetsuro Shinada、Yasutaka Yoshida、Yasufumi Ohfune

  DOI：10.1016/s0040-4039(98)01239-8

  日期：1998.8

  Exo-1,2-diols 3 and 4 were efficiently converted into the corresponding allyl sulfides by means of tri-n-butylphosphine (Bu3P) and diphenyl disulfide (PhS)(2). This method was applied to the introduction of a carbon-carbon double bond from diol 11 to give allyl sulfide 12 in a highly regioselective manner. The allyl sulfide 12 was transformed into (-)-shikimic acid (1) in four steps. (C) 1998 Elsevier Science Ltd. All rights reserved.