[(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 | 949000-01-5

• 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-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
• CAS: 949000-01-5
• 化学式: C₄₆H₄₈ClNO₁₃S
• 分子量: 890.405
• InChiKey: ITBMQTMSKYBQDD-UPSYKZGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  62
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  180
• 氢给体数：
  0
• 氢受体数：
  14

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-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 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 1.25h， 生成 [(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：

  N-benzyl-2-amino-6-O-benzyl-2,3-N,O-carbonyl-4-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl bromide 、 phenyl 2,3-di-O-acetyl-6-O-benzyl-1-thio-αb-D-galactopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 24.0h， 以56%的产率得到[(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
  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