3-(2',6'-difluorenylmethoxycarbonyl-3',4'-O-isopropylidene-α-D-galactopyranosyl)propanoylaminoethanoic acid | 808134-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-(2',6'-difluorenylmethoxycarbonyl-3',4'-O-isopropylidene-α-D-galactopyranosyl)propanoylaminoethanoic acid
• 英文别名: 2-[3-[(3aS,4R,6R,7S,7aS)-7-(9H-fluoren-9-ylmethoxycarbonyloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]propanoylamino]acetic acid
• CAS: 808134-33-0
• 化学式: C₄₄H₄₃NO₁₂
• 分子量: 777.825
• InChiKey: AHQYJQHKVLEZQS-FCDITBJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(2',6'-difluorenylmethoxycarbonyl-3',4'-O-isopropylidene-α-D-galactopyranosyl)propanoylaminoethanoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (Z)-2-[5-(2-{3-[(2R,3R,4S,5R,6R)-3-(9H-Fluoren-9-ylmethoxycarbonyloxy)-6-(9H-fluoren-9-ylmethoxycarbonyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yl]-propionylamino}-acetylamino)-pentyl]-but-2-enedioic acid 1-(2-cyano-ethyl) ester
  参考文献：
  名称：

  Facile Preparation of an Orthogonally Protected, pH-Sensitive, Bioconjugate Linker for Therapeutic Applications

  摘要：

  We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).

  DOI：

  10.1021/ol0483347
• 作为产物：
  描述：

  3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)propanoic acid 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 71.25h， 生成 3-(2',6'-difluorenylmethoxycarbonyl-3',4'-O-isopropylidene-α-D-galactopyranosyl)propanoylaminoethanoic acid
  参考文献：
  名称：

  Facile Preparation of an Orthogonally Protected, pH-Sensitive, Bioconjugate Linker for Therapeutic Applications

  摘要：

  We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).

  DOI：

  10.1021/ol0483347

文献信息

• Facile Preparation of an Orthogonally Protected, pH-Sensitive, Bioconjugate Linker for Therapeutic Applications
  作者：Steven Fletcher、Michael R. Jorgensen、Andrew D. Miller

  DOI：10.1021/ol0483347

  日期：2004.11.1

  We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).