tert-butyldimethylsilyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside | 1169693-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldimethylsilyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
• CAS: 1169693-56-4
• 化学式: C₅₈H₆₃NO₁₂Si
• 分子量: 994.223
• InChiKey: MXCLJWBODRQAQD-UERYBCNDSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.52
• 重原子数：
  72.0
• 可旋转键数：
  16.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  140.68
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 tert-butyldimethylsilyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates

  摘要：

  A short and high yielding synthesis of a core trisaccharide 1 as the key building block in the assembly of a library of N-glycan neoconjugates is presented. The beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage was introduced by inversion of the C-2 position of a beta-glucoside. The glucosyl donor was efficiently synthesised following a recently published one-pot strategy. 2-Naphthylmethyl and benzylidene-acetal protection in the terminal mannose permitted selective liberation of main branching sites for subsequent glycosylation. A C5 azido linker attached to the anomeric position, which is stable throughout the synthesis, will allow for the posterior immobilisation of deprotected glycans on a microarray surface. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.028
• 作为产物：
  描述：

  tert-butyldimethylsilyl 4,6-O-benzylidene-2-O-levulinoyl-3-O-(2-naphthylmethyl)-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside 在 乙酸肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到tert-butyldimethylsilyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates

  摘要：

  A short and high yielding synthesis of a core trisaccharide 1 as the key building block in the assembly of a library of N-glycan neoconjugates is presented. The beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage was introduced by inversion of the C-2 position of a beta-glucoside. The glucosyl donor was efficiently synthesised following a recently published one-pot strategy. 2-Naphthylmethyl and benzylidene-acetal protection in the terminal mannose permitted selective liberation of main branching sites for subsequent glycosylation. A C5 azido linker attached to the anomeric position, which is stable throughout the synthesis, will allow for the posterior immobilisation of deprotected glycans on a microarray surface. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.028