methyl 2-(acetylamino)-4-O-benzoyl-6-deoxy-3-O-<(2-methoxyethoxy)methyl>-6-(phenylseleno)-α-D-galactopyranoside | 137233-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(acetylamino)-4-O-benzoyl-6-deoxy-3-O-<(2-methoxyethoxy)methyl>-6-(phenylseleno)-α-D-galactopyranoside
• 英文别名: [(2S,3R,4R,5R,6S)-5-acetamido-6-methoxy-4-(2-methoxyethoxymethoxy)-2-(phenylselanylmethyl)oxan-3-yl] benzoate
• CAS: 137233-56-8
• 化学式: C₂₆H₃₃NO₈Se
• 分子量: 566.51
• InChiKey: CEUBLGLAEVOKCW-XCVFGXLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  101.55
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(acetylamino)-4-O-benzoyl-6-deoxy-3-O-<(2-methoxyethoxy)methyl>-6-(phenylseleno)-α-D-galactopyranoside 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 N-[(2S,3R,4R,5R)-5-[[[(2S,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-phenylselanylmethoxy]-dimethylsilyl]oxy-2-methoxy-4-(2-methoxyethoxymethoxy)-6-methylideneoxan-3-yl]acetamide
  参考文献：
  名称：

  Silicon-mediated reductive coupling of aldehydes and allylic alcohols. A stereoselective synthesis of tunicaminyluracil

  摘要：

  DOI：

  10.1021/ja00025a036
• 作为产物：
  描述：

  methyl 2-(acetylamino)-4,6-O-benzylidene-3-O-<(2-methoxyethoxy)methyl>-α-D-galactopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 四氯化碳 、 乙二醇二甲醚 为溶剂， 反应 20.0h， 生成 methyl 2-(acetylamino)-4-O-benzoyl-6-deoxy-3-O-<(2-methoxyethoxy)methyl>-6-(phenylseleno)-α-D-galactopyranoside
  参考文献：
  名称：

  Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V

  摘要：

  A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.

  DOI：

  10.1021/ja00090a018