[(3aR,4R,6R,7S,7aR)-3-benzyl-4-[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-6-hydroxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-oxo-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] 2-chloroacetate | 949000-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,4R,6R,7S,7aR)-3-benzyl-4-[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-6-hydroxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-oxo-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] 2-chloroacetate
• CAS: 949000-11-7
• 化学式: C₆₈H₆₉ClN₂O₂₀
• 分子量: 1269.75
• InChiKey: GXAJJOMHCJHQMG-VFVXHSQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  91
• 可旋转键数：
  29
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  249
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6R,7S,7aR)-3-benzyl-4-[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-6-hydroxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-oxo-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] 2-chloroacetate 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以92%的产率得到[(3aR,4R,6R,7S,7aR)-3-benzyl-4-[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-oxo-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] 2-chloroacetate
  参考文献：
  名称：

  Synthesis of a Natural Oligosaccharide Antibiotic Active against Helicobacter pylori

  摘要：

  An oligosaccharide active against Helicobacter pylori was synthesized in a highly efficient manner for the first time. The anti-H. pylori oligosaccharide structure is a core-2 branched-type oligosaccharide with a characteristic alpha-N-acetylglucosamine at the nonreducing end. The oligosaccharide was synthesized from the nonreducing end to the reducing end, with an N-benzyl-2,3-oxazolidinone-carrying glycosyl donor used to introduce an alpha-N-acetylglucosamine at the nonreducing end. Complete chemoselective activation of a bromo sugar in the presence of a thioglycoside acceptor was achieved, and the use of 2,6-dimethylphenyl thioglycoside prevented the aglycon transfer observed when the corresponding phenyl thioglycoside is used as an acceptor.

  DOI：

  10.1021/jo070669p
• 作为产物：
  描述：

  [(3aR,4R,6R,7S,7aR)-3-benzyl-4-[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-2-oxo-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] 2-chloroacetate 在 六氢-1-(苯基硫代)-2H-氮杂卓-2-酮 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸酐 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 1.08h， 生成 [(3aR,4R,6R,7S,7aR)-3-benzyl-4-[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-6-hydroxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-oxo-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] 2-chloroacetate
  参考文献：
  名称：

  Synthesis of a Natural Oligosaccharide Antibiotic Active against Helicobacter pylori

  摘要：

  An oligosaccharide active against Helicobacter pylori was synthesized in a highly efficient manner for the first time. The anti-H. pylori oligosaccharide structure is a core-2 branched-type oligosaccharide with a characteristic alpha-N-acetylglucosamine at the nonreducing end. The oligosaccharide was synthesized from the nonreducing end to the reducing end, with an N-benzyl-2,3-oxazolidinone-carrying glycosyl donor used to introduce an alpha-N-acetylglucosamine at the nonreducing end. Complete chemoselective activation of a bromo sugar in the presence of a thioglycoside acceptor was achieved, and the use of 2,6-dimethylphenyl thioglycoside prevented the aglycon transfer observed when the corresponding phenyl thioglycoside is used as an acceptor.

  DOI：

  10.1021/jo070669p