p-tolyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-1-thio-α-D-mannopyranoside | 1473360-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-2-(azidomethyl)-4,5-dibenzoyloxy-6-(4-methylphenyl)sulfanyloxan-3-yl] benzoate
• CAS: 1473360-07-4
• 化学式: C₃₄H₂₉N₃O₇S
• 分子量: 623.686
• InChiKey: UGROSEBFHOLEEK-MTXZWBDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-tolyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 生成 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-mannopyranose-1-O-trichloroacetimidate
  参考文献：
  名称：

  Synthesis and antiviral evaluation of 6′-acylamido-6′-deoxy-α-d-mannoglycerolipids

  摘要：

  Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute alpha-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.010
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-mannopyranose 在 甲醇 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 p-tolyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and antiviral evaluation of 6′-acylamido-6′-deoxy-α-d-mannoglycerolipids

  摘要：

  Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute alpha-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.010

文献信息

• Synthesis and antiviral evaluation of 6′-acylamido-6′-deoxy-α-d-mannoglycerolipids
  作者：Jun Zhang、Yihua Sun、Wei Wang、Xiaoshuang Zhang、Chunxia Li、Huashi Guan

  DOI：10.1016/j.carres.2013.08.010

  日期：2013.11

  Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute alpha-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9 mu M. (C) 2013 Elsevier Ltd. All rights reserved.