(2S,3S)-3-hydroxy-2-isobutylpent-4-enoic acid | 318957-90-3

• 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: (2S,3S)-3-hydroxy-2-isobutylpent-4-enoic acid
• CAS: 318957-90-3
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: BNBQQXBWCMRATM-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-hydroxy-2-isobutylpent-4-enoic acid 在 咪唑 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 28.75h， 生成 [(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-isobutyl-but-3-enyl]-carbamic acid tert-butyl 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 、 sodium hydroxide 、 Cx₂BOTf 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (2S,3S)-3-hydroxy-2-isobutylpent-4-enoic acid
  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

• Lipase-catalyzed Transesterification of Methyl 2-Substituted 3-Hydroxy-4-pentenoates and its Synthetic Application to the Taxol Side Chain
  作者：Tadakatsu Mandai、Tetsuta Oshitari、Masafumi Susowake

  DOI：10.1055/s-2002-34247

  日期：——

  Syn-and anti-methyl 2-substituted 3-hydroxy-4-pentenoates were efficiently resolved in lipase-catalyzed transesterification. This protocol was successfully applied to the synthesis of the taxol side chain.

  辛基和反式甲基2取代的3-羟基-4-戊烯酸酯在脂酶催化的转酯化反应中高效分离。该方法成功应用于紫杉醇侧链的合成。