2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride | 259236-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride
• 英文别名: (2R,3R,4S,5S,6R)-2-[(2S,3R,4R,5R,6R)-3-azido-2-fluoro-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 259236-41-4
• 化学式: C₅₄H₅₆FN₃O₉
• 分子量: 910.052
• InChiKey: CHCKKRNCXKVAEN-DLDWBHJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride 在 palladium dihydroxide 吡啶 、 二氯二茂锆 、 4 A molecular sieve 、 氢气 、 silver perchlorate 、 三乙胺 、 三氟乙酸 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 38.0h， 生成 N-(9H-fluoren-9-yl)methoxycarbonyl-O-(2-acetamido-2-deoxy-3-O-[β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-serine
  参考文献：
  名称：

  固相修饰的O-糖肽与癌症相关T抗原簇的固溶相合成。

  摘要：

  带有三个O-连接的T抗原的去唾液酸糖皮质激素AM的N-末端糖肽是通过“具有固相后处理的溶液相合成”，使用未保护的糖基氨基酸作为结构单元来制备的。对于糖肽组装，所有反应均在均相的NMP溶液中进行，而加入二乙醚后，每个反应的产物均易于分离为固体沉淀物。在构建模块的过程中，建立了一种鲁棒的方法来选择性地选择α-糖基化的Ser和Thr衍生物。[反应：看文字]

  DOI：

  10.1021/ol0514193
• 作为产物：
  描述：

  溴甲苯 、 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以81%的产率得到2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride
  参考文献：
  名称：

  Efficient and versatile synthesis of mucin-like glycoprotein mimics

  摘要：

  An efficient synthetic method of sequential glycopeptide-polymer by means of the combined chemical and enzymatic strategy was applied to the practical synthesis of some tandem repeating mucin-type glycoproteins. Versatility of the present synthetic strategy was demonstrated by elucidating some physicochemical and conformational analyses of these synthetic mucins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01359-5

文献信息

• Efficient and versatile synthesis of mucin-like glycoprotein mimics
  作者：Yuki Tachibana、Naoki Matsubara、Fumio Nakajima、Tetsuro Tsuda、Sakae Tsuda、Kenji Monde、Shin-Ichiro Nishimura

  DOI：10.1016/s0040-4020(02)01359-5

  日期：2002.12

  An efficient synthetic method of sequential glycopeptide-polymer by means of the combined chemical and enzymatic strategy was applied to the practical synthesis of some tandem repeating mucin-type glycoproteins. Versatility of the present synthetic strategy was demonstrated by elucidating some physicochemical and conformational analyses of these synthetic mucins. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Solution-Phase Synthesis with Solid-State Workup of an <i>O</i>-Glycopeptide with a Cluster of Cancer-Related T Antigens
  作者：Ning Shao、Zhongwu Guo

  DOI：10.1021/ol0514193

  日期：2005.8.1

  An N-terminal glycopeptide of asialoglycophorin AM with three O-linked T antigens was prepared by "solution-phase synthesis with solid-state workup" using unprotected glycosyl amino acids as building blocks. For the glycopeptide assembly, all reactions were conducted in homogeneous NMP solutions, while the product of each reaction was readily isolated as solid precipitates upon addition of diethyl

  带有三个O-连接的T抗原的去唾液酸糖皮质激素AM的N-末端糖肽是通过“具有固相后处理的溶液相合成”，使用未保护的糖基氨基酸作为结构单元来制备的。对于糖肽组装，所有反应均在均相的NMP溶液中进行，而加入二乙醚后，每个反应的产物均易于分离为固体沉淀物。在构建模块的过程中，建立了一种鲁棒的方法来选择性地选择α-糖基化的Ser和Thr衍生物。[反应：看文字]