phenyl 2-acetamido-3-O-benzoyl-2,4-di-deoxy-β-L-threo-hex-4-ene-dialdo-1,5-pyranoside | 404579-61-9

• 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: phenyl 2-acetamido-3-O-benzoyl-2,4-di-deoxy-β-L-threo-hex-4-ene-dialdo-1,5-pyranoside
• CAS: 404579-61-9
• 化学式: C₂₁H₁₉NO₆
• 分子量: 381.385
• InChiKey: CPBCBYOWPWFBCR-QKNQBKEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-acetamido-3-O-benzoyl-2,4-di-deoxy-β-L-threo-hex-4-ene-dialdo-1,5-pyranoside 在 四氮唑 、 叔丁基过氧化氢 、 ammonium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 生成 [[(2R,3R,4S)-3-acetamido-4-hydroxy-2-phenoxy-3,4-dihydro-2H-pyran-6-yl]-[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxymethyl]phosphonic acid
  参考文献：
  名称：

  Efficient Sialyltransferase Inhibitors Based on Glycosides of N-Acetylglucosamine

  摘要：

  D-Glucosamine was transformed into phenyl and 2-benzoyloxyethyl N-acetylglucosamine beta-glycosides 6a and 6b, respectively. Transformation of 6a,b into 6-O-unprotected N-acetylglucosamine derivatives 9a,b permitted the generation of an aldehyde group in the 6-position, Treatment of these intermediates with base afforded unsaturated aldehyde derivatives 10a,b, which are structural mimics of 2,3-dehydroneuraminic acid. H-Phosphonate addition to the aldehyde group and attachment of the cytidine monophosphate residue to the generated hydroxy group gave fully protected transition state analogues of cytidine monophosphate-N-acetylneuraminic acid 14a,b. Liberation of the unprotected compounds 1ah,l and 1lbh,l led to excellent inhibitors of alpha(2-6) -sialyltransferase from rat liver. Variation of the protective group cleavage procedure for 14a,b led to formal loss of phosphate, thus resulting in diene derivatives (E)-/(Z)-2a,b, which also exhibited inhibitory properties.

  DOI：

  10.1021/ja017370n
• 作为产物：
  描述：

  phenyl 2-acetamido-3,4-di-O-benzoyl-6-O-tertbutyldimethylsilyl-2-deoxy-β-D-glucopyranoside 在 吡啶 、 磷酸 、 乙酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 、 甲苯 为溶剂， 反应 72.33h， 生成 phenyl 2-acetamido-3-O-benzoyl-2,4-di-deoxy-β-L-threo-hex-4-ene-dialdo-1,5-pyranoside
  参考文献：
  名称：

  Efficient Sialyltransferase Inhibitors Based on Glycosides of N-Acetylglucosamine

  摘要：

  D-Glucosamine was transformed into phenyl and 2-benzoyloxyethyl N-acetylglucosamine beta-glycosides 6a and 6b, respectively. Transformation of 6a,b into 6-O-unprotected N-acetylglucosamine derivatives 9a,b permitted the generation of an aldehyde group in the 6-position, Treatment of these intermediates with base afforded unsaturated aldehyde derivatives 10a,b, which are structural mimics of 2,3-dehydroneuraminic acid. H-Phosphonate addition to the aldehyde group and attachment of the cytidine monophosphate residue to the generated hydroxy group gave fully protected transition state analogues of cytidine monophosphate-N-acetylneuraminic acid 14a,b. Liberation of the unprotected compounds 1ah,l and 1lbh,l led to excellent inhibitors of alpha(2-6) -sialyltransferase from rat liver. Variation of the protective group cleavage procedure for 14a,b led to formal loss of phosphate, thus resulting in diene derivatives (E)-/(Z)-2a,b, which also exhibited inhibitory properties.

  DOI：

  10.1021/ja017370n