(2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-3-methoxyoxolan-2-yl]-2-oxoethoxy]-4-[tert-butyl(dimethyl)silyl]oxy-3-(4-methylphenoxy)carbothioyloxy-N-[(3S)-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide | 258873-00-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-3-methoxyoxolan-2-yl]-2-oxoethoxy]-4-[tert-butyl(dimethyl)silyl]oxy-3-(4-methylphenoxy)carbothioyloxy-N-[(3S)-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide
• CAS: 258873-00-6
• 化学式: C₄₃H₆₅N₅O₁₃SSi₂
• 分子量: 948.252
• InChiKey: AOYUSBCBYQTLAS-LGUQQPKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  64
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  257
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-3-methoxyoxolan-2-yl]-2-oxoethoxy]-4-[tert-butyl(dimethyl)silyl]oxy-3-(4-methylphenoxy)carbothioyloxy-N-[(3S)-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 R-116022
  参考文献：
  名称：

  Novel Intramolecular Radical Ar-C Glycosylation-Lactonization Reaction in the Transformation of Capuramycin

  摘要：

  Radical deoxygenation of capuramycin derivative (2a,b) gave the unexpected lactone (3a,b) in moderate yield via a novel intramolecular radical Ar-C glycosylation-lactonization reaction. R-115381 and R-116022, thus obtained, showed weak antimicrobial activity against several Gram-positive bacteria.

  DOI：

  10.3987/com-99-s46
• 作为产物：
  描述：

  (4S,5S,6S)-6-[(1R)-2-氨基-1-[(2S,3S,4R,5R)-5-(2,4-二氧代嘧啶-1-基)-4-羟基-3-甲氧基四氢呋喃-2-基]-2-氧代乙氧基]-4,5-二羟基-N-[(3S)-2-氧代氮杂环庚-3-基]-5,6-二氢-4H-吡喃-2-甲酰胺 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-3-methoxyoxolan-2-yl]-2-oxoethoxy]-4-[tert-butyl(dimethyl)silyl]oxy-3-(4-methylphenoxy)carbothioyloxy-N-[(3S)-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide
  参考文献：
  名称：

  Novel Intramolecular Radical Ar-C Glycosylation-Lactonization Reaction in the Transformation of Capuramycin

  摘要：

  Radical deoxygenation of capuramycin derivative (2a,b) gave the unexpected lactone (3a,b) in moderate yield via a novel intramolecular radical Ar-C glycosylation-lactonization reaction. R-115381 and R-116022, thus obtained, showed weak antimicrobial activity against several Gram-positive bacteria.

  DOI：

  10.3987/com-99-s46

文献信息

• Novel Intramolecular Radical Ar-C Glycosylation-Lactonization Reaction in the Transformation of Capuramycin
  作者：Hitoshi Hotoda、Makiko Daigo、Toshio Takatsu、Akiko Muramatsu、Masakatsu Kaneko

  DOI：10.3987/com-99-s46

  日期：——

  Radical deoxygenation of capuramycin derivative (2a,b) gave the unexpected lactone (3a,b) in moderate yield via a novel intramolecular radical Ar-C glycosylation-lactonization reaction. R-115381 and R-116022, thus obtained, showed weak antimicrobial activity against several Gram-positive bacteria.