n-octyl 2-O-acetyl-3-azido-4,6-di-O-benzoyl-3-deoxy-β-D-galactopyranoside | 904285-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: n-octyl 2-O-acetyl-3-azido-4,6-di-O-benzoyl-3-deoxy-β-D-galactopyranoside
• CAS: 904285-72-9
• 化学式: C₃₀H₃₇N₃O₈
• 分子量: 567.639
• InChiKey: ZQYRUDQPUBNEMS-RQHKYSNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  41.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146.12
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  n-octyl 2-O-acetyl-3-azido-4,6-di-O-benzoyl-3-deoxy-β-D-galactopyranoside 在 三氟甲磺酸酐 甲醇 、 1-(苯基亚硫酰基)哌啶 、 4 A molecular sieve 、 sodium methylate 、 乙酰氯 、 2,4,6-三叔丁基嘧啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 53.87h， 生成 n-octyl 2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1->2)-3-azido-3-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of n-octyl 2,6-dideoxy-α-l-lyxo-hexopyranosyl-(1→2)-3-amino-3-deoxy-β-d-galactopyranoside, an analog of the H-disaccharide antigen

  摘要：

  The synthesis of an analog of the H-disaccharide antigen (2), in which the galactopyranosyl moiety bears an amino group at C-3 and the fucopyranosyl residue is deoxygenated at C-2, is reported. The key reaction in the preparation of 2 was the glycosylation of an appropriately protected n-octyl 3-azido-3-deoxy-galactopyranoside derivative with a 2,6-dideoxy thioglycoside promoted by 1-(phenylsulfinyl)piperidine and triflic anhydride. Disaccharide 2 is of interest in studies directed towards understanding the molecular basis of substrate recognition by the blood group A and B glycosyltransferases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.018
• 作为产物：
  描述：

  p-tolyl 2-O-acetyl-3-azido-4,6-di-O-benzoyl-3-deoxy-1-thio-β-D-galactopyranoside 、 辛醇 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以78%的产率得到n-octyl 2-O-acetyl-3-azido-4,6-di-O-benzoyl-3-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of n-octyl 2,6-dideoxy-α-l-lyxo-hexopyranosyl-(1→2)-3-amino-3-deoxy-β-d-galactopyranoside, an analog of the H-disaccharide antigen

  摘要：

  The synthesis of an analog of the H-disaccharide antigen (2), in which the galactopyranosyl moiety bears an amino group at C-3 and the fucopyranosyl residue is deoxygenated at C-2, is reported. The key reaction in the preparation of 2 was the glycosylation of an appropriately protected n-octyl 3-azido-3-deoxy-galactopyranoside derivative with a 2,6-dideoxy thioglycoside promoted by 1-(phenylsulfinyl)piperidine and triflic anhydride. Disaccharide 2 is of interest in studies directed towards understanding the molecular basis of substrate recognition by the blood group A and B glycosyltransferases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.018