3-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol | 288590-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol
• 英文别名: 3-hydroxypropyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside；1-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside)-1,3-dihydroxypropyl；3-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropan-1-ol
• CAS: 288590-07-8
• 化学式: C₃₇H₄₂O₇
• 分子量: 598.736
• InChiKey: QFRWWBAEINYTJX-DWCHZDDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(N,N-diethylamino)benzyl chloride 、 3-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol 在 四丁基溴化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 15.75h， 以89%的产率得到
  参考文献：
  名称：

  Structurally Simple Benzyl-Type Photolabile Protecting Groups for Direct Release of Alcohols and Carboxylic Acids

  摘要：

  Structurally simple benzyl-type photolabile protecting groups (PPGs) have been developed to release alcohols and carboxylic acids. Release of two substrates from one PPG chromophore has also been accomplished.

  DOI：

  10.1021/acs.orglett.5b00699
• 作为产物：
  描述：

  (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 在 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydroxide 、 水 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 68.0h， 以91%的产率得到3-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol
  参考文献：
  名称：

  簇状甘露糖苷作为 1 型菌毛介导的大肠杆菌粘附抑制剂：季戊四醇衍生物作为支架

  摘要：

  季戊四醇衍生物被用作合成两个簇状 α-D-甘露糖苷的核心分子，它们被设计为低聚甘露糖苷模拟物。寡甘露糖基化中经常出现的糖基原酸酯形成问题得到了解决。测试了这些簇在体外阻断大肠杆菌与酵母甘露聚糖结合的能力，发现其抑制甘露糖特异性粘附的能力是甲基 α-D-甘露糖苷的 200 多倍。

  DOI：

  10.1002/1099-0690(200006)2000:11<2027::aid-ejoc2027>3.0.co;2-l

文献信息

• Cluster Mannosides as Inhibitors of Type 1 Fimbriae-Mediated Adhesion ofEscherichia coli: Pentaerythritol Derivatives as Scaffolds
  作者：Thisbe K. Lindhorst、Michael Dubber、Ulrike Krallmann-Wenzel、Stefan Ehlers

  DOI：10.1002/1099-0690(200006)2000:11<2027::aid-ejoc2027>3.0.co;2-l

  日期：2000.6

  Pentaerythritol derivatives were used as core molecules for the synthesis of two cluster α-D-mannosides, which were designed as oligomannoside mimetics. The problem of glycosyl orthoester formation, which frequently occurs in oligo-mannosylations, was solved. The clusters were tested for their capacity to block binding of Escherichia coli to yeast mannan in vitro and were found to be more than 200

  季戊四醇衍生物被用作合成两个簇状 α-D-甘露糖苷的核心分子，它们被设计为低聚甘露糖苷模拟物。寡甘露糖基化中经常出现的糖基原酸酯形成问题得到了解决。测试了这些簇在体外阻断大肠杆菌与酵母甘露聚糖结合的能力，发现其抑制甘露糖特异性粘附的能力是甲基 α-D-甘露糖苷的 200 多倍。
• [EN] SYNTHETIC MOLECULES HAVING IMMUNE ACTIVITY<br/>[FR] MOLECULES SYNTHETIQUES A IMMUNO-ACTIVITE
  申请人：MALAGHAN INST OF MEDICAL RES

  公开号：WO2005049631A1

  公开（公告）日：2005-06-02

  The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosaccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.

  本发明涉及具有类似于PIM（酰基甘油磷脂肌醇寡糖）活性的合成分子，用于治疗和预防炎症性或免疫细胞介导的疾病或紊乱。
• Synthetic Molecules Having Immune Activity
  申请人：Singh-Gill Gurmit

  公开号：US20080249037A1

  公开（公告）日：2008-10-09

  The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosacccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.

  本发明涉及具有类似于PIM（酰基甘油磷酰肌醇低聚糖）活性的合成分子，用于治疗和预防由炎症或免疫细胞介导的疾病或障碍。
• US7989602B2
  申请人：——

  公开号：US7989602B2

  公开（公告）日：2011-08-02
• Structurally Simple Benzyl-Type Photolabile Protecting Groups for Direct Release of Alcohols and Carboxylic Acids
  作者：Pengfei Wang、Wenya Lu、Dattatray A. Devalankar、Zhenying Ding

  DOI：10.1021/acs.orglett.5b00699

  日期：2015.5.1

  Structurally simple benzyl-type photolabile protecting groups (PPGs) have been developed to release alcohols and carboxylic acids. Release of two substrates from one PPG chromophore has also been accomplished.