(2R,4S,5R,6R)-5-Acetylamino-6-((1R,2R)-3-azido-1,2-dihydroxy-propyl)-4-hydroxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 173911-66-5

• 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-hydroxy-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-hydroxy-2-(2-trimethylsilylethoxy)oxane-2-carboxylate
• CAS: 173911-66-5
• 化学式: C₁₇H₃₂N₄O₈Si
• 分子量: 448.549
• InChiKey: DOUHGAAXMSHJPI-WTUOYXTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  10

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-hydroxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 甲磺酰溴 、 sodium methylate 、 silver trifluoromethanesulfonate 、 镍 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 138.0h， 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)-5-Acetylamino-6-[(1R,2R)-1,2-dihydroxy-3-(toluene-4-sulfonyloxy)-propyl]-4-hydroxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium azide 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以83%的产率得到(2R,4S,5R,6R)-5-Acetylamino-6-((1R,2R)-3-azido-1,2-dihydroxy-propyl)-4-hydroxy-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