3-({1-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyl]allyloxy}dimethylsilanyloxy)-2-isobutylpent-4-enethioic acid S-benzyl ester | 318957-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-({1-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyl]allyloxy}dimethylsilanyloxy)-2-isobutylpent-4-enethioic acid S-benzyl ester
• CAS: 318957-51-6
• 化学式: C₄₁H₅₃NO₅SSi
• 分子量: 700.027
• InChiKey: DGRFIMZIQYRFHN-JMGLZSBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.91
• 重原子数：
  49.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-({1-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyl]allyloxy}dimethylsilanyloxy)-2-isobutylpent-4-enethioic acid S-benzyl ester 在 ruthenium carbene complex 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以69%的产率得到(R)-2-{(4R,7R)-7-[(R)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyl]-2,2-dimethyl-4,7-dihydro-[1,3,2]dioxasilepin-4-yl}-4-methyl-pentanethioic 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：

  (2R,3R)-3-Hydroxy-2-isobutyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 21.5h， 生成 3-({1-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyl]allyloxy}dimethylsilanyloxy)-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