2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl diphenyl phosphate | 1381864-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl diphenyl phosphate
• CAS: 1381864-50-1
• 化学式: C₂₇H₂₅ClN₃O₉P
• 分子量: 601.937
• InChiKey: YVHPFXUOVGJLML-OKFPMRFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  147.51
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl diphenyl phosphate 在 四氢呋喃 、 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 、 硫脲 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester
  参考文献：
  名称：

  A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures

  摘要：

  TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.059
• 作为产物：
  描述：

  2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-D-galactopyranose 、 氯磷酸二苯酯 在 N-甲基咪唑 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.08h， 以60%的产率得到2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl diphenyl phosphate
  参考文献：
  名称：

  A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures

  摘要：

  TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.059