(1S,2S)-(2-hydroxy-1-isobutylbut-3-enyl)-carbamic acid 9H-fluoren-9-ylmethyl ester | 318957-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (1S,2S)-(2-hydroxy-1-isobutylbut-3-enyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS: 318957-39-0
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: LDOOUNDUMVEWSR-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(2-hydroxy-1-isobutylbut-3-enyl)-carbamic acid 9H-fluoren-9-ylmethyl 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,3R,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：

  异己酰氯 在 吡啶 、 咪唑 、 sodium hydroxide 、 Cx₂BOTf 、 叠氮磷酸二苯酯 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.57h， 生成 (1S,2S)-(2-hydroxy-1-isobutylbut-3-enyl)-carbamic acid 9H-fluoren-9-ylmethyl 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

• Extensively Stereodiversified Scaffolds for Use in Diversity-Oriented Library Synthesis
  作者：Tiffany Malinky Gierasch、Zhangjie Shi、Gregory L. Verdine

  DOI：10.1021/ol027116f

  日期：2003.3.1

  represents an independently varied stereocenter. These scaffolds provide additional templates for investigations of geometric diversity in library syntheses. Libraries of these N-Fmoc-amino acids were further functionalized by incorporation into a peptide sequence, demonstrating the utility of 12 and 19 as building blocks for diversity oriented synthesis.

  报告了12和19的立体多样性库的合成，其中每个星号代表一个独立变化的立体中心。这些支架为研究文库合成中的几何多样性提供了额外的模板。这些N-Fmoc-氨基酸的文库通过掺入肽序列进一步功能化，证明了12和19作为多样性导向合成的基础材料的实用性。