(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropyl acetate | 131979-99-2

• 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: (S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropyl acetate
• 英文别名: (S)-3-acetoxy-1-(tert-butyldiphenylsiloxy)-2-methylpropane；[(2S)-3-[tert-butyl(diphenyl)silyl]oxy-2-methylpropyl] acetate
• CAS: 131979-99-2
• 化学式: C₂₂H₃₀O₃Si
• 分子量: 370.564
• InChiKey: ZPYIBQOUKUDMMT-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropyl acetate 在 咪唑 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 50.0h， 生成 (R)-3-[(tert-butyl)diphenylsilyloxy]-1-iodo-2-methylpropane
  参考文献：
  名称：

  芸苔素内酯的正式合成

  摘要：

  酶催化的C 2v形四醇-硫化物中羟基的分化，结合E-立体收敛的Ramberg-Bäcklund工艺，可以制备纯净的（2 S）-2,3-二甲基-1-碘丁烷加上3,5-环戊烯-20-硫代甲醇衍生物，以提供标题植物激素的有效前体。

  DOI：

  10.1016/s0040-4039(97)00474-7
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 以 氯仿 为溶剂， 生成 (S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropyl acetate
  参考文献：
  名称：

  An efficient chemo-enzymatic approach to the enantioselective synthesis of 2-methyl-1,3-propamedical derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)97925-5

文献信息

• Enantioselective transesterification of 2-methyl-1,3-propanediol derivatives catalyzed by Pseudomonas fluorescens lipase in an organic solvent
  作者：Paride Grisenti、Patrizia Ferraboschi、Ada Manzocchi、Enzo Santaniello

  DOI：10.1016/s0040-4020(01)92273-2

  日期：1992.1

  The irreversible transesterification of racemic 2-methyl-1,3-propanediol derivatives, the monoethers, 3a, 3b, 5a, and the monobenzoate 5b, with vinyl acetate catalyzed by Pseudomonas fluorescens lipase in chloroform affords enantiomerically pure chiral synthons.

  外消旋的2-甲基-1,3-丙二醇衍生物，单醚3a，3b，5a和单苯甲酸酯5b与氯乙烯假单胞菌脂肪酶催化的乙酸乙烯酯的不可逆酯交换反应提供对映体纯的手性合成子。
• Asymmetric total synthesis of (−)-rasfonin
  作者：Rajib Bhuniya、Samik Nanda

  DOI：10.1016/j.tet.2012.11.051

  日期：2013.1

  An efficient chemoenzymatic asymmetric synthesis of pyranone containing natural product (-)-rasfonin is presented here. Enantioselective enzymatic desymmetrization (EED) and a unique Gluconobacter oxydans mediated oxidative kinetic resolution (OKR) have been successfully employed to install three stereocenters (C-6', C-7, and C-9) of the target molecule. Stereoselective Achmatowicz reaction of a properly decorated furyl nucleus led to the core pyranone structure of rasfonin. At the late stage of the synthesis Negishi coupling has been used to complete the synthesis. (C) 2012 Elsevier Ltd. All rights reserved.
• Preparation of (2 R , 3 R , 4 R )-3-hydroxy-2,4,6-trimethylheptanoic acid via enzymatic desymmertization
  作者：Yoshinori Tokairin、Hiroyuki Konno

  DOI：10.1016/j.tet.2016.11.050

  日期：2017.1

  Synthesis of a unique fatty acyl unit to build the N-terminus of callipeltin A and homophymine B is described. Our approach to, access (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid uses enzymatic hydrolysis for the desymmetrization of achiral acetate, followed by diastereoselective Roush crotylboration and Wittig olefination for the backbone construction. (C) 2016 Elsevier Ltd. All rights reserved.
• Highly Stereo- and Regioselective Synthesis of (<i>Z</i>)-Trisubstituted Alkenes via 1-Bromo-1-alkyne Hydroboration−Migratory Insertion−Zn-Promoted Iodinolysis and Pd-Catalyzed Organozinc Cross-Coupling
  作者：Zhihong Huang、Ei-ichi Negishi

  DOI：10.1021/ja0772039

  日期：2007.11.28

  Hydroboration of 1-bromo-1-alkynes with dibromoborane followed by addition of 3 or 4 equiv of Me2Zn provides an efficient and selective route to (Z)-2-alkenyldimethylboranes (3) or (Z)-2-alkenylmethylzincs (4), respectively, which have been successfully applied to one-pot Suzuki (B-I) or Negishi (Zn-I) coupling in some less demanding cases. However, in more demanding cross-coupling reactions, only the use of either (Z)-2-alkenyliodides (5) or the alkenylzincs prepared from lithiation and then zincation of 5 proves to be highly satisfactory (Zn-II or Zn-III protocol). On the contrary, the corresponding organoboron coupling under B-II or B-III protocol appears to be less satisfactory. Preliminary studies indicate that certain substituents proximal to trisubstituted alkenes seriously affect the course of the desired alkenylboron crosscoupling.
• SANTANIELLO, E.;FERRABOSCHI, P.;GRISENTI, P., TETRAHEDRON LETT., 31,(1990) N9, C. 5651-5660
  作者：SANTANIELLO, E.、FERRABOSCHI, P.、GRISENTI, P.

  DOI：——

  日期：——