N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine phenacyl ester | 848701-29-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine phenacyl ester
• CAS: 848701-29-1
• 化学式: C₅₃H₅₄N₄O₁₉
• 分子量: 1051.03
• InChiKey: CUZJHCSUIHFXPW-NROXMFMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  76.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  291.04
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine phenacyl ester 、 乙酸酐 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以79%的产率得到N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine
  参考文献：
  名称：

  Synthesis of gold nanoparticles bearing the Thomsen–Friedenreich disaccharide: a new multivalent presentation of an important tumor antigen

  摘要：

  Herein we describe the synthesis gold nanoshells encapsulated with up to 90 units of the Thomsen-Friedenreich (TF) tumor-associated carbohydrate antigen (TACA) disaccharide (Galbeta1-3GaINAc-alpha-O-Ser/Thr) as well as the assembly of a suitably linked designer glycopeptide as a precursor to similar multivalent presentations on gold. The TF-coated nanoparticles are highly stable, water soluble, and easily handled. Improvements in the linker technology used to attach the disaccharide to the particles led to a robust multivalent platform for the presentation of this important carbohydrate. The antigen retains all recognition characteristics while displayed on this template as shown by several in vitro assays. This area of research could lead to the development of novel therapeutic agents that inhibit protein-carbohydrate interactions. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.12.003
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,4aR,7R,8R,8aR)-7-azido-6-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-serine phenacyl ester
  参考文献：
  名称：

  Synthesis of gold nanoparticles bearing the Thomsen–Friedenreich disaccharide: a new multivalent presentation of an important tumor antigen

  摘要：

  Herein we describe the synthesis gold nanoshells encapsulated with up to 90 units of the Thomsen-Friedenreich (TF) tumor-associated carbohydrate antigen (TACA) disaccharide (Galbeta1-3GaINAc-alpha-O-Ser/Thr) as well as the assembly of a suitably linked designer glycopeptide as a precursor to similar multivalent presentations on gold. The TF-coated nanoparticles are highly stable, water soluble, and easily handled. Improvements in the linker technology used to attach the disaccharide to the particles led to a robust multivalent platform for the presentation of this important carbohydrate. The antigen retains all recognition characteristics while displayed on this template as shown by several in vitro assays. This area of research could lead to the development of novel therapeutic agents that inhibit protein-carbohydrate interactions. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.12.003