tert-butyldimethyl[5-(tetrahydropyran-2-yloxy)pentyloxy]silane | 112906-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: tert-butyldimethyl[5-(tetrahydropyran-2-yloxy)pentyloxy]silane
• 英文别名: Tert-butyl-dimethyl-[5-(oxan-2-yloxy)pentoxy]silane
• CAS: 112906-40-8
• 化学式: C₁₆H₃₄O₃Si
• 分子量: 302.53
• InChiKey: YFMQYVIJIAAALV-UHFFFAOYSA-N

物化性质

• 沸点：
  345.1±37.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• 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-butyldimethyl[5-(tetrahydropyran-2-yloxy)pentyloxy]silane 在 phosphomolybdic acid 、 silica gel 作用下， 以 乙腈 为溶剂， 反应 0.42h， 以89%的产率得到1,5-戊二醇
  参考文献：
  名称：

  A Facile, Catalytic, and Environmentally Benign Method for Selective Deprotection of tert-Butyldimethylsilyl Ether Mediated by Phosphomolybdic Acid Supported on Silica Gel

  摘要：

  An environmentally benign PMA supported on SiO2 is found to be an efficient catalyst for the chemoselective deprotection of TBDMS ethers under very mild conditions. Various labile functional groups such as isopropylidene acetal, OTBDPS, OTHP, Oallyl, OBn, alkene, alkyne, OAc, OBz, N-Boc, N-Cbz, N-Fmoc, mesylate, and azide are found to be stable under the reaction conditions. This "truly catalytic" heterogeneous reaction does not require aqueous workup, and the supported catalyst and the solvent can be readily recovered and recycled.

  DOI：

  10.1021/jo0502697
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 5-(叔丁基二甲基硅杂氧基)-1-戊醇 在 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 8.0h， 以84%的产率得到tert-butyldimethyl[5-(tetrahydropyran-2-yloxy)pentyloxy]silane
  参考文献：
  名称：

  InCl3 immobilized in ionic liquids: a novel and recyclable catalytic system for tetrahydropyranylation and furanylation of alcohols

  摘要：

  一种温和且高效的方法已被开发，用于在温和条件下使用少量氯化铟固定在1-丁基-3-甲基咪唑四氟磷酸盐离子液体中保护羟基化合物，形成四氢吡喃醚和呋喃醚。多种官能团和保护基，如THP、TBDMS、TBDPS、PMB、MOM醚、丙烯醇和环氧化物，与离子液体兼容。该新方法还实现了二醇的单保护。

  DOI：

  10.1039/b210044b

文献信息

• Cupric sulfate pentahydrate (CuSO4·5H2O): a mild and efficient catalyst for tetrahydropyranylation/depyranylation of alcohols and phenols
  作者：Abu T. Khan、Lokman H. Choudhury、Subrata Ghosh

  DOI：10.1016/j.tetlet.2004.08.141

  日期：2004.10

  Various alcohols and phenols can be smoothly converted to the corresponding THP ethers using 20 mol % CuSO4·5H2O under mild reaction conditions at room temperature. Some of the major advantages of this procedure are nonaqueous work-up, very good yields, less expensive catalyst and compatibility with other protecting groups.

  在室温下，在温和的反应条件下，使用20 mol％的CuSO 4 ·5H 2 O可将各种醇和酚平稳地转化为相应的THP醚。该方法的一些主要优点是非水后处理，非常好的收率，较便宜的催化剂以及与其他保护基的相容性。
• A Novel and Chemoselective Transformation of Alcohol Silyl Ethers into the Corresponding Tetrahydropyranyl Ethers
  作者：Takeshi Suzuki、Takeshi Oriyama

  DOI：10.1055/s-2001-12343

  日期：——

  Direct conversion of alcohol silyl ethers into the corresponding tetrahydropyranyl (THP) ethers can be easily performed by reaction with THP acetate under the influence of a catalytic amount of tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf). Aliphatic TBS ether can be selectively transformed into the corresponding THP ether in the presence of phenolic TBS ether.

  在一定量的三氟甲磺酸叔丁基二甲基硅烷（TBSOTf）催化剂的作用下，通过与乙酸四氢吡喃酯（THP）反应，可以很容易地将醇硅醚直接转化为相应的四氢吡喃（THP）醚。脂肪族 TBS 醚可在酚类 TBS 醚的存在下选择性地转化为相应的 THP 醚。
• Tetrabutylammonium Tribromide (TBATB)−MeOH:  An Efficient Chemoselective Reagent for the Cleavage of <i>tert</i>-Butyldimethylsilyl (TBDMS) Ethers
  作者：Rangam Gopinath、Bhisma K. Patel

  DOI：10.1021/ol006720s

  日期：2000.12.1

  [GRAPHICS]TBDMS, THP, and DMT ethers are efficiently deprotected with tetrabutylammonium tribromide in methanol, The apparent order of stability of different protecting group is phenolic TBDMS > 1 degrees OTBDPS > 2 degrees OTBDMS > 2 degrees OTHP > 1 degrees OTHP > 1 degrees OTBDMS > 1 degrees ODMT. TBDMS ether has been cleaved selectively in the presence of isopropylidine, an, Ac, Bz, THP, and TBDPS groups. This method is high yielding, fast, clean, safe, cost effective, and therefore most suitable for practical organic synthesis.
• A catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol is a good combination for the cleavage of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers
  作者：Abu T. Khan、Samimul Islam、Lokman H. Choudhury、Subrata Ghosh

  DOI：10.1016/j.tetlet.2004.11.011

  日期：2004.12

  Various THP and TBS ethers can be unmasked easily to the corresponding hydroxyl compounds in good yields by using a combination of a catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol at room temperature. In addition, alkyl TBS ethers can be hydrolyzed chemo selectively in the presence of aryl TBS ethers. Moreover, alkyl TBS ethers can be cleaved easily in the presence of alkyl or aryl THP ethers using the same conditions. (C) 2004 Published by Elsevier Ltd.
• A facile and catalytic method for selective deprotection of tert-butyldimethylsilyl ethers with copper(II) bromide
  作者：Suchitra Bhatt、Sandip K. Nayak

  DOI：10.1016/j.tetlet.2006.09.073

  日期：2006.11

  Copper(H) bromide is found to be a simple and efficient catalyst for selective deprotection of tert-butyidimethylsilyl ethers of alcohols/phenols at ambient temperature. Various labile functional groups such as ketal, alkene, ketone, OTBDPS, OTHP and allyl and benzyl ethers are found to be compatible under the reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.