[(2S,3R,4S,5S,6R)-3-acetyloxy-2-(2,6-dimethylphenyl)sulfanyl-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl] acetate | 948999-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5S,6R)-3-acetyloxy-2-(2,6-dimethylphenyl)sulfanyl-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl] acetate
• CAS: 948999-99-3
• 化学式: C₂₅H₃₀O₇S
• 分子量: 474.575
• InChiKey: PBQWNAAUACYCFL-JAWPICGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5S,6R)-3-acetyloxy-2-(2,6-dimethylphenyl)sulfanyl-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl] acetate 在 六氢-1-(苯基硫代)-2H-氮杂卓-2-酮 、 2,6-二叔丁基-4-甲基吡啶 、 硼烷四氢呋喃络合物 、 三氟甲磺酸酐 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 [(3aR,4R,6R,7S,7aR)-3-benzyl-4-[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-[(2R,3R,4R,5R,6S)-5-azido-2-(hydroxymethyl)-6-methoxy-3-phenylmethoxyoxan-4-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：

  2,6-dimethylphenyl 4,6-O-benzylidene-1-thio-β-galactopyranoside 在 吡啶 、 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 [(2S,3R,4S,5S,6R)-3-acetyloxy-2-(2,6-dimethylphenyl)sulfanyl-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl] acetate
  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