diallyl [phenyl 2-acetamido-3-O-benzoyl-2,4-dideoxy-β-L-threo-hex-4-enopyranoside-6-yl]-phosphonate | 404579-63-1

• 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: diallyl [phenyl 2-acetamido-3-O-benzoyl-2,4-dideoxy-β-L-threo-hex-4-enopyranoside-6-yl]-phosphonate
• 英文别名: [(2R,3R,4S)-3-acetamido-6-[bis(prop-2-enoxy)phosphoryl-hydroxymethyl]-2-phenoxy-3,4-dihydro-2H-pyran-4-yl] benzoate
• CAS: 404579-63-1
• 化学式: C₂₇H₃₀NO₉P
• 分子量: 543.51
• InChiKey: BINLFCJMYHEBQB-IPEIQGKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diallyl [phenyl 2-acetamido-3-O-benzoyl-2,4-dideoxy-β-L-threo-hex-4-enopyranoside-6-yl]-phosphonate 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  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：

  苯基-N-乙酰基-beta-D-氨基葡糖苷 在 吡啶 、 4-二甲氨基吡啶 、 磷酸 、 三乙胺 、 乙酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 79.16h， 生成 diallyl [phenyl 2-acetamido-3-O-benzoyl-2,4-dideoxy-β-L-threo-hex-4-enopyranoside-6-yl]-phosphonate
  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

文献信息

• Efficient Sialyltransferase Inhibitors Based on Glycosides of <i>N</i>-Acetylglucosamine
  作者：Ralf Schwörer、Richard R. Schmidt

  DOI：10.1021/ja017370n

  日期：2002.2.1

  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.