Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-4-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester | 363139-24-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-4-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3S,4S,5R,6S)-5-acetyloxy-4-azido-6-[(2S,3R,4R,5S,6S)-2-[(2S,3R,4R,5S,6S)-2-ethylsulfanyl-6-methyl-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-5-methoxy-6-methyl-3-phenylmethoxyoxan-4-yl]oxy-2-methyloxan-3-yl] acetate
• CAS: 363139-24-6
• 化学式: C₄₆H₅₉N₃O₁₃S
• 分子量: 894.053
• InChiKey: VKGDGMZYUNGPMN-QNTQNNEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  p-Nitrophenyl endo-3,4-O-benzylidene-6-deoxy-2-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-talopyranoside 、 Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-4-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以69%的产率得到
  参考文献：
  名称：

  Synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serovar 17

  摘要：

  Effective synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serovar 17 in a p-aminophenyl linker-containing form, using 3+2 block synthesis strategy, is described. A 2+3 block synthesis could not be achieved, although different glycosyl donors (1-Br, 1-SPh, 1-O-C(NH)CCl3) were used. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00934-0
• 作为产物：
  描述：

  3-azido-3-deoxy-1,2-O-isopropylidene-6-O-(p-toluenesulfonyl)-α-D-glucofuranose 在 六甲基磷酰三胺 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 溴 、 乙酸肼 、 sodium cyanoborohydride 、 sodium iodide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-4-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serovar 17

  摘要：

  Effective synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serovar 17 in a p-aminophenyl linker-containing form, using 3+2 block synthesis strategy, is described. A 2+3 block synthesis could not be achieved, although different glycosyl donors (1-Br, 1-SPh, 1-O-C(NH)CCl3) were used. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00934-0