(2S,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester | 244177-72-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester
• 英文别名: S-benzyl (2S,3R)-3-hydroxy-2-(2-methylpropyl)pent-4-enethioate
• CAS: 244177-72-8
• 化学式: C₁₆H₂₂O₂S
• 分子量: 278.415
• InChiKey: OEODUJCAKHNZIC-LSDHHAIUSA-N

物化性质

• 沸点：
  395.1±42.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 N-羟基-7-氮杂苯并三氮唑 、 Hoveyda-Grubbs catalyst second generation 、 tetra-n-propylammonium perruthenate. 、 双氧水 、 N-甲基吗啉氧化物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 89.83h， 生成 (+)-丁苯那嗪
  参考文献：
  名称：

  A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine

  摘要：

  A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-alpha-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.

  DOI：

  10.1021/ol301612q
• 作为产物：
  描述：

  4-甲基戊酸 在 正丁基锂 、 三甲基铝 、 三甲基乙酰氯 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.92h， 生成 (2S,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester
  参考文献：
  名称：

  A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine

  摘要：

  A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-alpha-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.

  DOI：

  10.1021/ol301612q

文献信息

• The Synthesis of an Exhaustively Stereodiversified Library of <i>cis</i>-1,5 Enediols by Silyl-Tethered Ring-Closing Metathesis
  作者：Bryce A. Harrison、Gregory L. Verdine

  DOI：10.1021/ol0159569

  日期：2001.7.1

  [reaction: see text] This report describes the parallel synthesis of all 16 stereoisomers of the cis-1,5 enediol module 1. Compounds 1 derive from 2 by silicon-tethered ring-closing metathesis. Such libraries of stereodiversified ligands provide a unique approach to ligand discovery that employs exhaustive searching of conformational space.

  [反应：参见文本]该报告描述了顺式1,5烯二醇模块1的所有16种立体异构体的平行合成。化合物1通过硅束缚的开环复分解反应从2衍生而来。这种立体多样化配体的文库提供了独特的方法来进行配体发现，该方法采用了构象空间的详尽搜索。
• A Modular Synthetic Approach toward Exhaustively Stereodiversified Ligand Libraries
  作者：Tiffany Malinky Gierasch、Milan Chytil、Mary T. Didiuk、Julie Y. Park、Jeffrey J. Urban、Steven P. Nolan、Gregory L. Verdine

  DOI：10.1021/ol006560k

  日期：2000.12.1

  This report describes a modular approach to the synthesis of stereodiversified natural product like libraries. Monomers 2 and 3 were coupled in parallel by silyl tethered olefin metathesis to generate all 16 stereoisomers of cis-enediols 1. All 16 stereoisomers were incorporated into chimerae having flanking peptidic segments. These chimerae exhibited a broad range of hydrophobicities, raising the possibility that stereochemical variation might be used to tune the pharmacologic properties of small molecules.
• A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine
  作者：Manuel Johannes、Karl-Heinz Altmann

  DOI：10.1021/ol301612q

  日期：2012.7.20

  A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-alpha-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.