(2R,4S,5R,6R)-5-Acetylamino-6-((1R,2R)-3-azido-1,2-dihydroxy-propyl)-4-benzoyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 173911-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-5-Acetylamino-6-((1R,2R)-3-azido-1,2-dihydroxy-propyl)-4-benzoyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-6-[(1R,2R)-3-azido-1,2-dihydroxypropyl]-4-benzoyloxy-2-(2-trimethylsilylethoxy)oxane-2-carboxylate
• CAS: 173911-67-6
• 化学式: C₂₄H₃₆N₄O₉Si
• 分子量: 552.657
• InChiKey: FQNGQUWGCCZYMX-IPSPCLKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  155
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-5-Acetylamino-6-((1R,2R)-3-azido-1,2-dihydroxy-propyl)-4-benzoyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 甲磺酰溴 、 sodium methylate 、 silver trifluoromethanesulfonate 、 镍 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 42.0h， 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：

  (2R,4S,5R,6R)-4-Acetoxy-6-[(1R,2R)-1-acetoxy-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-5-acetylamino-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 叠氮化锂 、 15-冠醚-5 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 122.0h， 生成 (2R,4S,5R,6R)-5-Acetylamino-6-((1R,2R)-3-azido-1,2-dihydroxy-propyl)-4-benzoyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  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

文献信息

• Synthesis of a Bis(sialic acid) 8,9-Lactam
  作者：Teddy Ercégovic、Göran Magnusson

  DOI：10.1021/jo950994p

  日期：1996.1.1

  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).