tert-butyl-[(1S)-1-[(4S,5R,6S)-2-cyclohexyl-5-methyl-6-propan-2-yl-1,3,2-dioxaborinan-4-yl]ethoxy]-dimethylsilane | 491589-43-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: tert-butyl-[(1S)-1-[(4S,5R,6S)-2-cyclohexyl-5-methyl-6-propan-2-yl-1,3,2-dioxaborinan-4-yl]ethoxy]-dimethylsilane
• CAS: 491589-43-6
• 化学式: C₂₁H₄₃BO₃Si
• 分子量: 382.467
• InChiKey: AUFNVOCWYUHAEJ-UMGGQSCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(1S)-1-[(4S,5R,6S)-2-cyclohexyl-5-methyl-6-propan-2-yl-1,3,2-dioxaborinan-4-yl]ethoxy]-dimethylsilane 在 4-甲基苯磺酸吡啶 双氧水 、 sodium acetate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 (2S,3R,4R,5S)-2-O-tert-butyldimethylsilyl-3,5-O-isopropyliden-4,6-dimethyl-2,3,5-heptanetriol
  参考文献：
  名称：

  Stereoselective synthesis of syn,syn-2-methyl-1,3-diols through one-pot aldol–reduction sequence

  摘要：

  Chx(2)BCl-inediated syn-aldol reaction of the alpha-OTBS lactate-derived ketone 1 followed by in situ reduction of the resulting boron aldolate with LiBH4 lead to complete stereoselectivity for the bororlates 2 in 80-95% yields. Then, a very mild oxidative work-up of 2 (H2O2/NaOAc in THF-H2O) allows isolation of syn,syn-2-methyl-1,3-diols 3 in yields up to 95% without migration of the TBS group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01289-3
• 作为产物：
  描述：

  氯代二环己基硼烷 、 异丁醛 、 3-戊酮,2-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-,(2S)- 在 三乙胺 、 锂硼氢 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 3.5h， 以95%的产率得到tert-butyl-[(1S)-1-[(4S,5R,6S)-2-cyclohexyl-5-methyl-6-propan-2-yl-1,3,2-dioxaborinan-4-yl]ethoxy]-dimethylsilane
  参考文献：
  名称：

  Stereoselective synthesis of syn,syn-2-methyl-1,3-diols through one-pot aldol–reduction sequence

  摘要：

  Chx(2)BCl-inediated syn-aldol reaction of the alpha-OTBS lactate-derived ketone 1 followed by in situ reduction of the resulting boron aldolate with LiBH4 lead to complete stereoselectivity for the bororlates 2 in 80-95% yields. Then, a very mild oxidative work-up of 2 (H2O2/NaOAc in THF-H2O) allows isolation of syn,syn-2-methyl-1,3-diols 3 in yields up to 95% without migration of the TBS group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01289-3

文献信息

• Stereoselective synthesis of syn,syn-2-methyl-1,3-diols through one-pot aldol–reduction sequence
  作者：Marta Galobardes、Marisa Mena、Pedro Romea、Fèlix Urpı́、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(02)01289-3

  日期：2002.8

  Chx(2)BCl-inediated syn-aldol reaction of the alpha-OTBS lactate-derived ketone 1 followed by in situ reduction of the resulting boron aldolate with LiBH4 lead to complete stereoselectivity for the bororlates 2 in 80-95% yields. Then, a very mild oxidative work-up of 2 (H2O2/NaOAc in THF-H2O) allows isolation of syn,syn-2-methyl-1,3-diols 3 in yields up to 95% without migration of the TBS group. (C) 2002 Elsevier Science Ltd. All rights reserved.