(2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid amide | 193223-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid amide
• CAS: 193223-11-9
• 化学式: C₂₁H₄₃NO₆Si₂
• 分子量: 461.747
• InChiKey: HPBNSZQTDYMXGC-YTGMWSOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  100.24
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid amide 在 三氟甲磺酸三甲基硅酯 、 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以15%的产率得到allyl 3,4-di-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-2-O-tert-butyldimethylsilyl-β-D-glucopyranosiduronamide
  参考文献：
  名称：

  A Moenomycin-type Structural Analogue of Lipid II some possible mechanisms of the mode of action of transglycosylase inhibitors can be discarded

  摘要：

  The transglycosylation step in the peptidoglycan biosynthesis belongs to the general class of glycosyltransferase-catalyzed reactions. The structural analogue 2 of moenomycin A has been synthesized and has been found to be antibiotically inactive. The assumption that moenomycin-type transglycosylase inhibitors such as 1 bind at the donor site of the enzyme and that their mode of action is the result of the high stability of the sugar --> phosphate bond seems to be ruled out by the present results.

  DOI：

  10.1002/prac.19973390162
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid amide 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以72%的产率得到(2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid amide
  参考文献：
  名称：

  A Moenomycin-type Structural Analogue of Lipid II some possible mechanisms of the mode of action of transglycosylase inhibitors can be discarded

  摘要：

  The transglycosylation step in the peptidoglycan biosynthesis belongs to the general class of glycosyltransferase-catalyzed reactions. The structural analogue 2 of moenomycin A has been synthesized and has been found to be antibiotically inactive. The assumption that moenomycin-type transglycosylase inhibitors such as 1 bind at the donor site of the enzyme and that their mode of action is the result of the high stability of the sugar --> phosphate bond seems to be ruled out by the present results.

  DOI：

  10.1002/prac.19973390162