(2R,3S)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester | 318957-32-3

• 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: (2R,3S)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester
• CAS: 318957-32-3
• 化学式: C₁₆H₂₂O₂S
• 分子量: 278.415
• InChiKey: OEODUJCAKHNZIC-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester 在 ruthenium carbene complex 氢氟酸 作用下， 以 四氢呋喃 、 吡啶 、 甲苯 为溶剂， 反应 6.0h， 生成 (2R,3S,6S,7S)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester
  参考文献：
  名称：

  A Modular Synthetic Approach toward Exhaustively Stereodiversified Ligand Libraries

  摘要：

  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.

  DOI：

  10.1021/ol006560k
• 作为产物：
  描述：

  (4R,5S)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-oxazolidin-2-one 在 三氟甲磺酸二丁硼 、 三甲基铝 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 (2R,3S)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester
  参考文献：
  名称：

  A Modular Synthetic Approach toward Exhaustively Stereodiversified Ligand Libraries

  摘要：

  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.

  DOI：

  10.1021/ol006560k

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。