(3S,4R,5S,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diol | 307492-69-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (3S,4R,5S,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diol
• 英文别名: (E,3S,4R,5S,6S)-7-[tert-butyl(diphenyl)silyl]oxy-4,6-dimethyl-1-phenylhept-1-ene-3,5-diol
• CAS: 307492-69-9
• 化学式: C₃₁H₄₀O₃Si
• 分子量: 488.742
• InChiKey: HNHQVCGSKOUNQU-IIRIOQIMSA-N

物化性质

• 沸点：
  587.5±50.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (3S,4R,5S,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diol 在 4-甲基苯磺酸吡啶 作用下， 反应 2.0h， 以80%的产率得到tert-butyldiphenyl((S)-2-((4S,5R,6S)-2,2,5-trimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)propoxy)silane
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin D

  摘要：

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

  DOI：

  10.1021/jo047732k
• 作为产物：
  描述：

  (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 tin(II) trifluoromethanesulfonate 、 2,3-dichloro-4,5-dicyanoquinone 、 二异丁基氢化铝 、 sodium tartrate 、 溶剂黄146 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 44.0h， 生成 (3S,4R,5S,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diol
  参考文献：
  名称：

  （+）-crocacin C的全合成

  摘要：

  遵循收敛策略，实现了光学纯形式的（+）-crocacin C（3）的首次合成。合成还建立了这种新型的有效抗真菌和高细胞毒性化合物的绝对立体化学。天然存在的卡洛卡因C具有（6 S，7 S，8 R，9 S）构型，对于该家族的其他同类产品，卡洛卡星A，B和D也是相同的。

  DOI：

  10.1016/s0040-4039(00)02002-5

文献信息

• Total synthesis of (+)-crocacin C
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.bmc.2010.03.003

  日期：2010.6.1

  Two approaches toward the total synthesis of cytotoxic polyketide natural product (+)-crocacin C (1) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans' chiral propionimide (5% overall yield). No protecting groups were utilized in the total synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.
• Step-Economic Synthesis of (+)-Crocacin C: A Concise Crotylboronation/[3,3]-Sigmatropic Rearrangement Approach
  作者：Adele E. Pasqua、Frank D. Ferrari、Chris Hamman、Yanzhou Liu、James J. Crawford、Rodolfo Marquez

  DOI：10.1021/jo301210f

  日期：2012.8.17

  The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.
• Asymmetric total synthesis of the myxobacteria metabolites crocacins A–D
  作者：John T. Feutrill、Michael J. Lilly、Jonathan M. White、Mark A. Rizzacasa

  DOI：10.1016/j.tet.2008.01.139

  日期：2008.5

  The total syntheses of crocacins A-D are described. The key steps were a syn-aldol reaction followed by anti-reduction to secure the stereo-tetrad and acylation of an ene- or dienecarbamate to form the enamide. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.
• Total Synthesis of (+)-Crocacin C
  作者：Luiz C. Dias、Luciana G. de Oliveira

  DOI：10.1021/ol016845c

  日期：2001.11.1

  [GRAPHICS]The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me2CuCNLi2 and a Stille cross-coupling between E-vinyl stannane 5 and E-vinyl iodide 6 to establish the (E,E)-dienamide moiety.
• Total Synthesis of (+)-Crocacin D
  作者：Luiz C. Dias、Luciana G. de Oliveira、Janaína D. Vilcachagua、Florian Nigsch

  DOI：10.1021/jo047732k

  日期：2005.3.1

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.