(R)-(3-tert-butyldimethylsiloxy)-5-(pivaloyloxy)-1-pentanol | 104629-71-2

• 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)-(3-tert-butyldimethylsiloxy)-5-(pivaloyloxy)-1-pentanol
• 英文别名: (3R)-3-(Tert-butyldimethylsilyloxy)-5-pivaloyloxypentanol；[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-hydroxypentyl] 2,2-dimethylpropanoate
• CAS: 104629-71-2
• 化学式: C₁₆H₃₄O₄Si
• 分子量: 318.529
• InChiKey: FQTAHDDRQJYHQC-CYBMUJFWSA-N

物化性质

• 沸点：
  364.8±37.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(3-tert-butyldimethylsiloxy)-5-(pivaloyloxy)-1-pentanol 在 甲醇 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 3 A molecular sieve 、 三苯基膦 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one
  参考文献：
  名称：

  阿维菌素b 1a螺缩醛单元的对映体合成

  摘要：

  阿维菌素B 1a的螺缩醛单元（C 15 -C 28）已通过利用立体控制的贝克酵母还原法进行对映体特异性合成。

  DOI：

  10.1016/s0040-4039(00)85191-6
• 作为产物：
  描述：

  1-(6-bornylidene)-3-(tert-butyldimethylsiloxy)-4-pentene 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (R)-(3-tert-butyldimethylsiloxy)-5-(pivaloyloxy)-1-pentanol
  参考文献：
  名称：

  Optically active ketones as chiral auxiliaries in the [2,3]-Wittig rearrangement

  摘要：

  The stereochemical aspects of the [2,3]-Wittig rearrangement of optically active tertiary allyl ethers derived from (+)-camphor and (-)-fenchone were investigated. The rearrangement of the (+)-camphor derivative yielded two olefin products in a 70/30 E/Z ratio. The geometry of the trisubstituted olefin produced during the rearrangement was assigned by NOE experiments. The configuration of the newly formed carbinol center of the products was established by kinetic resolution, Mosher's method, and conversion to derivatives of known absolute configuration. The absolute configuration of the carbinol center for the Z isomer was assigned to be S and that of the E isomer to be R. The (-)-fenchone derivative gave only a single Z olefin product, which was assigned the S configuration at the carbinol center.

  DOI：

  10.1021/jo00003a048

文献信息

• Trifunctional Chiral Synthons via Stereocontrolled Yeast Reduction. Preparation of Chiral Pentane-1,3,5-triol Derivatives
  作者：Masahiro Hirama、Takeshi Nakamine、Shô Itô

  DOI：10.1246/cl.1986.1381

  日期：1986.8.5

  Easy access to pentane-1,3,5-triol derivatives of high optical purity, trifunctional chiral synthons of fundamental importance in the synthesis of various natural products is described, as well as the stereocontrol of baker’s yeast reduction of 5-substituted 3-oxopentanoates.

  描述了容易获得高光学纯度的戊烷-1,3,5-三醇衍生物，在各种天然产物的合成中具有根本重要性的三官能手性合成子，以及面包酵母还原 5-取代 3-氧代戊酸酯的立体控制.
• KEEGAN, DAVID S.;MIDLAND, M. MARK;WERLEY, RALPH T.;MCLOUGHLIN, JIM I., J. ORG. CHEM., 56,(1991) N, C. 1185-1191
  作者：KEEGAN, DAVID S.、MIDLAND, M. MARK、WERLEY, RALPH T.、MCLOUGHLIN, JIM I.

  DOI：——

  日期：——
• Enantiospecific synthesis of the spiroacetal unit of avermectin b1a
  作者：Masahiro Hirama、Takeshi Nakamine、Shô Itô

  DOI：10.1016/s0040-4039(00)85191-6

  日期：1986.1

  The spiroacetal unit (C15−C28) of avermectin B1a has been enantiospecifically synthesized by taking advantage of stereocontrolled baker's yeast reduction.

  阿维菌素B 1a的螺缩醛单元（C 15 -C 28）已通过利用立体控制的贝克酵母还原法进行对映体特异性合成。
• Optically active ketones as chiral auxiliaries in the [2,3]-Wittig rearrangement
  作者：David S. Keegan、M. Mark Midland、Ralph T. Werley、Jim I. McLoughlin

  DOI：10.1021/jo00003a048

  日期：1991.2

  The stereochemical aspects of the [2,3]-Wittig rearrangement of optically active tertiary allyl ethers derived from (+)-camphor and (-)-fenchone were investigated. The rearrangement of the (+)-camphor derivative yielded two olefin products in a 70/30 E/Z ratio. The geometry of the trisubstituted olefin produced during the rearrangement was assigned by NOE experiments. The configuration of the newly formed carbinol center of the products was established by kinetic resolution, Mosher's method, and conversion to derivatives of known absolute configuration. The absolute configuration of the carbinol center for the Z isomer was assigned to be S and that of the E isomer to be R. The (-)-fenchone derivative gave only a single Z olefin product, which was assigned the S configuration at the carbinol center.