[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-isobutyl-but-3-enyl]-carbamic acid 9H-fluoren-9-ylmethyl ester | 244177-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-isobutyl-but-3-enyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS: 244177-78-4
• 化学式: C₂₉H₄₁NO₃Si
• 分子量: 479.735
• InChiKey: WBSJFAKEYHJVSZ-RRPNLBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-isobutyl-but-3-enyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 在 ruthenium carbene complex 氢氟酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 水 、 甲苯 为溶剂， 反应 10.0h， 生成 (2R,3R,6R,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：

  在 lithium hydroxide 、 叠氮磷酸二苯酯 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 10.5h， 生成 [(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-isobutyl-but-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