(R)-5-(tert-butyldimethylsilyl)oxy-4-methyl-1-pentanol | 143728-66-9

• 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: (R)-5-(tert-butyldimethylsilyl)oxy-4-methyl-1-pentanol
• 英文别名: (R)-S75-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol；(4R)-5-[tert-butyl(dimethyl)silyl]oxy-4-methylpentan-1-ol
• CAS: 143728-66-9
• 化学式: C₁₂H₂₈O₂Si
• 分子量: 232.439
• InChiKey: RVWUQHAPWDLLLB-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  15
• 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：

  (R)-5-(tert-butyldimethylsilyl)oxy-4-methyl-1-pentanol 在 吡啶 、 manganese(IV) oxide 、 正丁基锂 、 草酰氯 、 lithium (1 percent sodium) 、 四丁基氟化铵 、 氨 、 sodium 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 calcium carbonate 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 丁酮 为溶剂， 反应 77.92h， 生成 (R)-debromoneoaplaminone
  参考文献：
  名称：

  Absolute stereochemistry of aplaminone and neoaplaminone, cytotoxic bromodopamines from a marine mollusc: enantioselective synthesis of debromoneoaplaminone

  摘要：

  The absolute stereochemistry of potent cytotoxic bromodopamines, aplaminone and neoaplaminone has been determined by means of enantioselective synthesis of debromoneoaplaminone, a derivative of aplaminone and neoaplaminone.

  DOI：

  10.1016/s0040-4039(00)74687-9
• 作为产物：
  描述：

  <4S,3(2R)>-4-benzyl-3-<4-(tert-butoxycarbonyl)-2-methylbutanoyl>-2-oxazolidinone 在 咪唑 、 lithium aluminium tetrahydride 、 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (R)-5-(tert-butyldimethylsilyl)oxy-4-methyl-1-pentanol
  参考文献：
  名称：

  Stereoselective Synthesis of Rapamycin Fragment To Build a Macrocyclic Toolbox

  摘要：

  A stereoselective synthesis of a rapamycin fragment is developed and further utilized toward building a macrocyclic chemical toolbox. The amino alcohol moiety embedded in the 22-membered macrocyclic ring allowed for the addition of a variation in the chiral side chain. The key reactions leading to the synthesis of the rapamycin-derived pyran fragment include the following: (i) Paterson aldol, (ii) stereoselective β-OH carbonyl reduction, and (iii) regio- and stereoselective intramolecular oxy-Michael reaction. The other piece needed for building the macrocyclic diversity was obtained from the coupling of various amino alcohol moieties with S-pipecolic acid.

  DOI：

  10.1021/ol5034833

文献信息

• Synthesis of a C1−C21 Subunit of the Protein Phosphatase Inhibitor Tautomycin:  A Formal Total Synthesis
  作者：James A. Marshall、Mathew M. Yanik

  DOI：10.1021/jo0056951

  日期：2001.2.1

  The synthesis of a C1-C21 subunit of tautomycin is described. The convergent route employs enantioenriched allenylstannane and zinc reagents derived from (S)-3-butyn-2-ol methanesulfonate. These reagents react with appropriate aldehyde segments to yield syn and anti adducts with high diastereoselectivity. The derived lithioalkynes are joined stepwise to a CO equivalent, (MeONMe)2C=O, to afford an intermediate

  描述了互变霉素C1-C21亚基的合成。收敛路线采用了对映体富集的烯丙基锡烷和衍生自（S）-3-butyn-2-ol甲磺酸盐的锌试剂。这些试剂与适当的醛链段反应，以高非对映选择性产生顺式和反加合物。将衍生的硫代炔烃逐步连接至CO当量（MeONMe）2 C ＝ O，以提供中间体酮，该中间体酮在酸处理后转化为互变异构体的核心螺缩酮部分。通过将上述烯丙基锌试剂另一种添加到螺酮醛中来进行链延长，以高非对映选择性进行，以安装剩余的立体中心。所得的炔丙醇加合物通过炔烃的分子内氢化硅烷化和衍生的五元硅氧烷的Tamoo氧化而转化为甲基酮。该酮被证明与张伯林在先前的互变异构全合成中使用的中间体相同。
• Absolute stereochemistry of aplaminone and neoaplaminone, cytotoxic bromodopamines from a marine mollusc: enantioselective synthesis of debromoneoaplaminone
  作者：Hideo Kigoshi、Yuichi Adachi、Kohji Yoshikawa、Kiyoyuki Yamada

  DOI：10.1016/s0040-4039(00)74687-9

  日期：1992.7

  The absolute stereochemistry of potent cytotoxic bromodopamines, aplaminone and neoaplaminone has been determined by means of enantioselective synthesis of debromoneoaplaminone, a derivative of aplaminone and neoaplaminone.
• Stereoselective Synthesis of Rapamycin Fragment To Build a Macrocyclic Toolbox
  作者：Shiva Krishna Reddy Guduru、Ravikumar Jimmidi、Girdhar Singh Deora、Prabhat Arya

  DOI：10.1021/ol5034833

  日期：2015.2.6

  A stereoselective synthesis of a rapamycin fragment is developed and further utilized toward building a macrocyclic chemical toolbox. The amino alcohol moiety embedded in the 22-membered macrocyclic ring allowed for the addition of a variation in the chiral side chain. The key reactions leading to the synthesis of the rapamycin-derived pyran fragment include the following: (i) Paterson aldol, (ii) stereoselective β-OH carbonyl reduction, and (iii) regio- and stereoselective intramolecular oxy-Michael reaction. The other piece needed for building the macrocyclic diversity was obtained from the coupling of various amino alcohol moieties with S-pipecolic acid.