(2S,3S,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal | 85828-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal
• 英文别名: (2S,3S,4S)-3-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethyl-5-phenylmethoxypentanal
• CAS: 85828-12-2
• 化学式: C₂₀H₃₄O₃Si
• 分子量: 350.574
• InChiKey: AEEPIQVHLBMFBQ-ZIFCJYIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal 在 氢氟酸 、 叔丁基锂 、 间氯过氧苯甲酸 作用下， 生成 (1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one
  参考文献：
  名称：

  Total synthesis of tirandamycin. A short, efficient synthesis of the Ireland alcohol

  摘要：

  DOI：

  10.1021/jo00160a044
• 作为产物：
  描述：

  (R)-3-(benzyloxy)-2-methylpropan-1-ol 在 (+)-Ipc₂BOMe 、 四氧化锇 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 高碘酸 、 三乙胺 作用下， 反应 25.25h， 生成 (2S,3S,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid and determination of the absolute stereochemistry of the natural product from callipeltin A

  摘要：

  A revised stereostructure of 3-hydroxy-2,4,6-trimethylheptanoic acid, the beta-hydroxy acid that acylates the N-terminus of callipeltin A. is proposed on the basis of analysis of J-coupling in the H-1 NMR spectrum of the acetonide derivative obtained front the acid hydrolysate of callipeltin A. The proposed Structure was definitively confirmed by enantioselective synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00328-2

文献信息

• Manipulation of the aldol adducts from lactate-derived ketones. A versatile chiral auxiliary for the asymmetric synthesis of β-hydroxy carbonyl compounds
  作者：Ian Paterson、Debra J. Wallace

  DOI：10.1016/0040-4039(94)88435-8

  日期：1994.11

  The ketones 1 and 2 can be transformed into a wide range of enantiomerically-pure anti and syn α-methyl-β-hydroxy ketones and aldehydes. The α′-methyl group in 5 and 11 may be retained, demonstrating the use of the lactate-derived group as an optional chiral auxiliary.

  酮1和2可以转化到广泛范围的对映体纯的抗和顺式α甲基β羟基酮和醛。可以保留5和11中的α'-甲基，这表明使用乳酸酯衍生的基团作为任选的手性助剂。
• Synthesis of the dioxabicyclononane unit of tirandamycin
  作者：T.Rose Kelly、Nizal S. Chandrakumar、John D. Cutting、R.Richard Goehring、Franz R. Weibel

  DOI：10.1016/s0040-4039(00)98954-8

  日期：1985.1
• A total synthesis of (.+-.)-tirandamycin B
  作者：Stephen J. Shimshock、Robert E. Waltermire、Philip DeShong

  DOI：10.1021/ja00023a029

  日期：1991.11

  The total synthesis of the dienoyl tetramic acid antibiotic (+/-)-tirandamycin B is described. The key transformations of the strategy include (1) cyclization of pyranone 14 with fluorosilicic acid to provide the 2,6-dioxabicyclo[3.3.1]nonane system of the natural product, (2) reductive removal of the benzyl ether from enone 15, and (3) attachment of the tetramic acid moiety by using the Schlessinger phosphonate protocol. Protection of the primary hydroxyl function of tirandamycin B as the triisopropylsilyl (TIPS) ether was crucial to the success of the strategy.
• Asymmetric Catalysis Route to <i>anti</i>,<i>anti</i> Stereotriads, Illustrated by Applications
  作者：Kathlyn A. Parker、Qiuzhe Xie

  DOI：10.1021/ol702989g

  日期：2008.4.1

  A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.
• Stereoselective synthesis of (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid and determination of the absolute stereochemistry of the natural product from callipeltin A
  作者：Angela Zampella、Maria Valeria D'Auria

  DOI：10.1016/s0957-4166(02)00328-2

  日期：2002.7

  A revised stereostructure of 3-hydroxy-2,4,6-trimethylheptanoic acid, the beta-hydroxy acid that acylates the N-terminus of callipeltin A. is proposed on the basis of analysis of J-coupling in the H-1 NMR spectrum of the acetonide derivative obtained front the acid hydrolysate of callipeltin A. The proposed Structure was definitively confirmed by enantioselective synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.