(1R,2R)-(2-hydroxy-1-isobutylbut-3-enyl)-carbamic acid 9H-fluoren-9-ylmethyl ester | 318957-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (1R,2R)-(2-hydroxy-1-isobutylbut-3-enyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl N-[(3R,4R)-3-hydroxy-6-methylhept-1-en-4-yl]carbamate
• CAS: 318957-40-3
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: LDOOUNDUMVEWSR-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-(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 5.0h， 生成 (2R,3R,6R,7R)-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：

  (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 咪唑 、 sodium hydroxide 、 叠氮磷酸二苯酯 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.57h， 生成 (1R,2R)-(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

• 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.