(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhexan-3-ol | 153788-89-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhexan-3-ol
• 英文别名: (2R,3R,4R)-1-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylhexan-3-ol
• CAS: 153788-89-7
• 化学式: C₁₄H₃₂O₂Si
• 分子量: 260.492
• InChiKey: KJGGZNWTXIGADN-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhexan-3-ol 在 manganese(IV) oxide 、 四丁基氟化铵 、 二异丁基氢化铝 、 N,N'-硫羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (E,6S,8R)-4,6,8-trimethyldec-4-en-1-yn-3-one
  参考文献：
  名称：

  Studies of novel cyclitols. A synthesis of 3′O,4′O-dimethylfuniculosin

  摘要：

  A synthesis of funiculosin dimethyl ether (2) is described. Methodologies for an asymmetric conjugate addition to establish the 1,3-anti dimethyl array, stereocontrolled formation of the Z,E-bis-allylic C-11 alcohol, and interception of a reactive pyridinone methide are examined. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01496-9
• 作为产物：
  描述：

  (2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol 在 Rh/Al₂O₃ 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhexan-3-ol
  参考文献：
  名称：

  Studies of novel cyclitols. A synthesis of 3′O,4′O-dimethylfuniculosin

  摘要：

  A synthesis of funiculosin dimethyl ether (2) is described. Methodologies for an asymmetric conjugate addition to establish the 1,3-anti dimethyl array, stereocontrolled formation of the Z,E-bis-allylic C-11 alcohol, and interception of a reactive pyridinone methide are examined. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01496-9

文献信息

• Construction of 4-Hydroxy-2-pyridinones. Total Synthesis of (+)-Sambutoxin
  作者：David R. Williams、Regis A. Turske

  DOI：10.1021/ol006410+

  日期：2000.10.1

  [GRAPHICS]Total synthesis of (+)-sambutoxin has been achieved, establishing the relative and absolute stereochemistry of the naturally occurring mycotoxin, Efforts feature methodology for enantiocontrolled construction of 1,3-anti dimethyl arrays and a novel Saegusa oxidation to provide a pyridinone methide leading to formation of the central dihydropyran ring.
• Studies of novel cyclitols. A synthesis of 3′O,4′O-dimethylfuniculosin
  作者：David R Williams、Patrick D Lowder、Yu-Gui Gu

  DOI：10.1016/s0040-4039(00)01496-9

  日期：2000.12

  A synthesis of funiculosin dimethyl ether (2) is described. Methodologies for an asymmetric conjugate addition to establish the 1,3-anti dimethyl array, stereocontrolled formation of the Z,E-bis-allylic C-11 alcohol, and interception of a reactive pyridinone methide are examined. (C) 2000 Published by Elsevier Science Ltd.
• A synthesis of (−)-ebelactones A and B
  作者：John P. Cooksey、Rhonan Ford、Philip J. Kocieński、Beatrice Pelotier、Jean-Marc Pons

  DOI：10.1016/j.tet.2010.05.072

  日期：2010.8

  A synthesis of the beta-lactone esterase inhibitors (-)-ebelactones A and B is described. The synthesis features the use of a Hoppe homoaldol reaction and a Cu(I)-mediated 1,2-metallate rearrangement of a metallated enol carbamate as key fragment linkage reactions. (C) 2010 Elsevier Ltd. All rights reserved.