(1R,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol | 162956-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 162956-98-1
• 化学式: C₁₈H₃₆O₆Si
• 分子量: 376.566
• InChiKey: ABVYPSLOAWKTBK-KBUPBQIOSA-N

物化性质

• 沸点：
  424.0±45.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  25
• 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：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 在 溴化二甲基溴化锍 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以99%的产率得到甘露醇
  参考文献：
  名称：

  使用 Nafion-H®/碘化钠（或溴化二甲基溴化锍）在甲醇中对叔丁基二甲基甲硅烷基醚进行选择性脱保护

  摘要：

  摘要 溴化二甲基溴化锍或 Nafion-H 以及 NaI（1 当量）在甲醇中的催化量可轻松以高产率裂解各种 TBDMS 醚。与酚类 TBDMS 醚、苄基和甲基醚相比，烷基 TBDMS 醚更容易和选择性地反应。

  DOI：

  10.1081/scc-120026345
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 双丙酮-D-甘露糖醇 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到(1R,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
  参考文献：
  名称：

  Diastereoselective Grignard Additions to O-Protected Polyhydroxylated Ketones:  A Reaction Controlled by Groundstate Conformation?

  摘要：

  The O-protected polyhydroxy ketones 9-14 and 39, 42 add sigma-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-28 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the ''top face'' of the carbonyl group is much less shielded than the ''bottom'' face. Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.

  DOI：

  10.1021/jo961542v

文献信息

• An Efficient Synthesis of Enantiopure 1-Alkoxy-1,2-propadienes from Propargyl Bromide
  作者：Patrick Rochet、Jean-Michel Vatèle、Jacques Goré

  DOI：10.1055/s-1994-25577

  日期：——

  A number of enantiopure functionalized alcohols have been O-allenylated by reaction of their corresponding sodium alcoholates with propargyl bromide followed by t-BuOK catalyzed isomerization of the resulting propargyl ethers, in good overall yields.

  一系列对映纯功能化醇通过其相应钠醇盐与丙炔溴化物反应后，再经过t-BuOK催化的异构化反应，对得到的丙炔醚进行O-烯丙基化，获得了良好的总体产率。
• Diastereoselective Grignard Additions to <i>O</i>-Protected Polyhydroxylated Ketones:  A Reaction Controlled by Groundstate Conformation?
  作者：Johann Mulzer、Catarina Pietschmann、Jürgen Buschmann、Peter Luger

  DOI：10.1021/jo961542v

  日期：1997.6.13

  The O-protected polyhydroxy ketones 9-14 and 39, 42 add sigma-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-28 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the ''top face'' of the carbonyl group is much less shielded than the ''bottom'' face. Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.
• Selective Deprotection of <b> <i>tert</i> </b>-Butyldimethylsilyl Ethers Using Nafion-H®/Sodium Iodide (or Bromodimethylsulfonium Bromide) in Methanol
  作者：Shikha Rani、J. Lokesh Babu、Yashwant D. Vankar

  DOI：10.1081/scc-120026345

  日期：2003.12.1

  Catalytic amounts of bromodimethyl sulfonium bromide, or Nafion-H along with NaI (1 equiv.), in methanol cleave a variety of TBDMS ethers readily in high yields. Alkyl TBDMS ethers react more readily and selectively compared to phenolic TBDMS ethers, benzyl, and methyl ethers.

  摘要 溴化二甲基溴化锍或 Nafion-H 以及 NaI（1 当量）在甲醇中的催化量可轻松以高产率裂解各种 TBDMS 醚。与酚类 TBDMS 醚、苄基和甲基醚相比，烷基 TBDMS 醚更容易和选择性地反应。