methyl (2-(trimethylsilyl)ethyl 5-acetamido-9-azido-4-O-benzoyl-3,5,9-trideoxy-8-O-{methyl [5-acetamido-4,7,8,9-tetra-O-acetyl-3-(phenylthio)-3,5-dideoxy-D-erythro-α-L-gluco-2-nonulopyranosid]onate}-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 173911-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2-(trimethylsilyl)ethyl 5-acetamido-9-azido-4-O-benzoyl-3,5,9-trideoxy-8-O-{methyl [5-acetamido-4,7,8,9-tetra-O-acetyl-3-(phenylthio)-3,5-dideoxy-D-erythro-α-L-gluco-2-nonulopyranosid]onate}-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2S,3S,4R,5S,6R)-5-acetamido-2-[(1R,2R)-1-[(2R,3R,4S,6R)-3-acetamido-4-benzoyloxy-6-methoxycarbonyl-6-(2-trimethylsilylethoxy)oxan-2-yl]-3-azido-1-hydroxypropan-2-yl]oxy-4-acetyloxy-3-phenylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 173911-72-3
• 化学式: C₅₀H₆₇N₅O₂₁SSi
• 分子量: 1134.25
• InChiKey: JUGPTRHEWFAFGH-QUPDRXIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  78
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  339
• 氢给体数：
  3
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  methyl (2-(trimethylsilyl)ethyl 5-acetamido-9-azido-4-O-benzoyl-3,5,9-trideoxy-8-O-{methyl [5-acetamido-4,7,8,9-tetra-O-acetyl-3-(phenylthio)-3,5-dideoxy-D-erythro-α-L-gluco-2-nonulopyranosid]onate}-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 sodium methylate 、 镍 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 40.0h， 生成 methyl (2R,4S,5R,6R)-5-acetamido-6-[(R)-[(2R,6R,8R,9R,10S)-9-acetamido-10-hydroxy-5-oxo-8-[(1R,2R)-1,2,3-trihydroxypropyl]-1,7-dioxa-4-azaspiro[5.5]undecan-2-yl]-hydroxymethyl]-4-hydroxy-2-(2-trimethylsilylethoxy)oxane-2-carboxylate
  参考文献：
  名称：

  Synthesis of a Bis(sialic acid) 8,9-Lactam

  摘要：

  Methyl [2-(trimethylsilyl)ethyl 5-acetamido-9-azido-4-O-benzoyl-3,5,9-trideoxy-D-glycero-alpha-D-galacto- 2-nonulopyranosid]onate was sialylated with methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-thio-3-(phenylthio)- 2,3,5-trideoxy-D-erythro-alpha-L-gluco-2-nonulopyranosid)onate to give the corresponding bis(sialic acid) derivative in 23% yield. Removal of protecting groups, reduction of the azido group to an amino group, and removal of the auxiliary thiophenyl group gave the desired bis(sialic acid) 8,9-lactam. Comparison of the H-1 NMR spectra and energy-minimized (MM3) structures of the bis(sialic acid) lactam with those of the corresponding bis(sialic acid) lactone showed the conformations of the two compounds to be very similar (RMS = 0.027 Angstrom).

  DOI：

  10.1021/jo950994p
• 作为产物：
  描述：

  Methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 在 吡啶 、 叠氮化锂 、 15-冠醚-5 、 甲磺酰溴 、 sodium methylate 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 68.0h， 生成 methyl (2-(trimethylsilyl)ethyl 5-acetamido-9-azido-4-O-benzoyl-3,5,9-trideoxy-8-O-{methyl [5-acetamido-4,7,8,9-tetra-O-acetyl-3-(phenylthio)-3,5-dideoxy-D-erythro-α-L-gluco-2-nonulopyranosid]onate}-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of a Bis(sialic acid) 8,9-Lactam

  摘要：

  Methyl [2-(trimethylsilyl)ethyl 5-acetamido-9-azido-4-O-benzoyl-3,5,9-trideoxy-D-glycero-alpha-D-galacto- 2-nonulopyranosid]onate was sialylated with methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-thio-3-(phenylthio)- 2,3,5-trideoxy-D-erythro-alpha-L-gluco-2-nonulopyranosid)onate to give the corresponding bis(sialic acid) derivative in 23% yield. Removal of protecting groups, reduction of the azido group to an amino group, and removal of the auxiliary thiophenyl group gave the desired bis(sialic acid) 8,9-lactam. Comparison of the H-1 NMR spectra and energy-minimized (MM3) structures of the bis(sialic acid) lactam with those of the corresponding bis(sialic acid) lactone showed the conformations of the two compounds to be very similar (RMS = 0.027 Angstrom).

  DOI：

  10.1021/jo950994p