Toluene-4-sulfonic acid (1S,3aR,4R,5S,7aS)-1-tert-butoxy-4-hydroxy-7a-methyl-octahydro-inden-5-yl ester | 898528-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid (1S,3aR,4R,5S,7aS)-1-tert-butoxy-4-hydroxy-7a-methyl-octahydro-inden-5-yl ester
• CAS: 898528-29-5
• 化学式: C₂₁H₃₂O₅S
• 分子量: 396.548
• InChiKey: IZGAXQBPGVNZSG-HZKQSDJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (1S,3aR,4R,5S,7aS)-1-tert-butoxy-4-hydroxy-7a-methyl-octahydro-inden-5-yl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  An Expedited Approach to the Vitamin D trans-Hydrindane Building Block from the Hajos Dione

  摘要：

  Efficient and operationally simple synthesis of the key trans-hydrindane alcohol building block for the synthesis of calicitriol (1 alpha,25-dihydroxyvitamin D(3)) has been developed. Epoxy alcohol prepared almost quantitatively from the Hajos dione was reduced at the quaternary carbon by the Hutchins procedure (NaBH(3)CN-BF(3)(.)Et(2)O). The diol was selectively deoxygenized either using the Barton-McCombie reaction (with Bu(3)SnH-AIBN) or via the respective iodohydrine (with LiAlH(4)).

  DOI：

  10.1021/ol060775y
• 作为产物：
  描述：

  4,5-O,O'-diacetyl-(1S,3aR,4R,5S,7aS)-1-tert-butoxy-7a-methyloctahydro-1H-indene-4,5-diol 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 Toluene-4-sulfonic acid (1S,3aR,4R,5S,7aS)-1-tert-butoxy-4-hydroxy-7a-methyl-octahydro-inden-5-yl ester
  参考文献：
  名称：

  An Expedited Approach to the Vitamin D trans-Hydrindane Building Block from the Hajos Dione

  摘要：

  Efficient and operationally simple synthesis of the key trans-hydrindane alcohol building block for the synthesis of calicitriol (1 alpha,25-dihydroxyvitamin D(3)) has been developed. Epoxy alcohol prepared almost quantitatively from the Hajos dione was reduced at the quaternary carbon by the Hutchins procedure (NaBH(3)CN-BF(3)(.)Et(2)O). The diol was selectively deoxygenized either using the Barton-McCombie reaction (with Bu(3)SnH-AIBN) or via the respective iodohydrine (with LiAlH(4)).

  DOI：

  10.1021/ol060775y