(-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester | 175550-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: (2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-1-(tert-butyloxycarbonyl)-5-(n-nonyl)pyrrolidine；tert-butyl (2S,3S,5R)-2-benzyl-3-[tert-butyl(dimethyl)silyl]oxy-5-nonylpyrrolidine-1-carboxylate
• CAS: 175550-96-6
• 化学式: C₃₁H₅₅NO₃Si
• 分子量: 517.868
• InChiKey: BWPUAEBKOXEANJ-PKTNWEFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.14
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 [(2S,3S,5R)-2-benzyl-1-methyl-5-nonylpyrrolidin-3-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  A Concise Stereoselective Synthesis of Preussin, 3-epi-Preussin, and Analogues

  摘要：

  A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.

  DOI：

  10.1021/ol0606435
• 作为产物：
  描述：

  癸醛 在 palladium diacetate 、 双(2-二苯基磷苯基)醚 咪唑 、 盐酸 、 titanium(IV) tetraethanolate 、 sodium hydroxide 、 copper bromide dimethyl sulfide complex 、 臭氧 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.0h， 生成 (-)-(2S,3S,5R)-2-benzyl-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A Concise Stereoselective Synthesis of Preussin, 3-epi-Preussin, and Analogues

  摘要：

  A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.

  DOI：

  10.1021/ol0606435

文献信息

• A Flexible Approach to (<i>S</i>)-5-Alkyl Tetramic Acid Derivatives:  Application to the Asymmetric Synthesis of (+)-Preussin and Protected (3<i>S</i>,4<i>S</i>)-AHPPA
  作者：Pei-Qiang Huang、Tian-Jun Wu、Yuan-Ping Ruan

  DOI：10.1021/ol035617a

  日期：2003.11.1

  text] A flexible asymmetric approach to 5-alkyl tetramic acid derivatives is described, which is based on the use of 9 as the first synthetic equivalent to chiral nonracemic tetramic acid 5-carbanionic synthon 9b. The existence of the carbanion intermediate 9b was proven by trapping with trimethylchlorosilane. Application of the present method to the synthesis of antifungal alkaloid (+)-preussin, as well

  [反应：见正文]描述了一种对5-烷基四甲基酸衍生物的灵活的不对称方法，该方法基于使用9作为手性非外消旋四甲酸5-碳双离子合成子9b的第一个合成等价物。通过用三甲基氯硅烷捕获证明了碳负离子中间体9b的存在。还描述了本方法在抗真菌生物碱（+）-普鲁酶和受保护的（3S，4S）-AHPPA 6的合成中的应用。
• A concise and efficient synthesis of (+)-preussin
  作者：Enzo B. Arévalo-García

  DOI：10.1515/hc-2013-0236

  日期：2014.2.1

  A novel and efficient synthesis of (+)-preussin (7) starting from N-butoxycarbonyl-L-phenylalaninal (1) is described. This natural product was synthesized under mild conditions and with good overall yield.

  摘要：本文介绍了一种从N-丁氧羰基-L-苯丙氨酸醛（1）出发，高效、温和地合成（+）-普鲁辛（7）的新方法。该天然产物的总收率较好。
• Novel Route to the Synthesis of Hydroxylated Pyrrolidine Derivatives via the Intramolecular Reaction of g-Aminoallylstannane with Aldehyde. Total Synthesis of (+)-Preussin
  作者：Yoshinori Yamamoto、Isao Kadota、Shioko Saya

  DOI：10.3987/com-97-s19

  日期：——
• A novel stereoselective synthesis of enantiomerically pure antifungal agent, (+)-preussin
  作者：Hidemi Yoda、Hiroyasu Yamazaki、Kunihiko Takabe

  DOI：10.1016/0957-4166(96)00009-2

  日期：1996.2

  An efficient and novel process is described for the asymmetric synthesis of (2S,3S,SR)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, (+)-preussin employing reductive deoxygenation of a functionalized quaternary alpha-hydroxy N-Boc pyrrolidine obtained by stereocontrolled elaboration of tri-O-benzyl-beta-D-arabinofuranose. The synthetic strategy involves no separation of stereoisomers through the entire sequence.
• A Concise Stereoselective Synthesis of Preussin, 3-<i>e</i><i>pi</i>-Preussin, and Analogues
  作者：Myra Beaudoin Bertrand、John P. Wolfe

  DOI：10.1021/ol0606435

  日期：2006.5.1

  A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.