(2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-((5-bromo-7-methylspiro[indole-3,2'-[1,3]dioxan]-2-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate | 1163260-34-1

• 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: (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-((5-bromo-7-methylspiro[indole-3,2'-[1,3]dioxan]-2-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS: 1163260-34-1
• 化学式: C₂₆H₃₁BrN₂O₁₁
• 分子量: 627.443
• InChiKey: CYDLWWYGRITVQU-LBRNTXKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  157.28
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  5-bromo-7-methyl-3,3-(trimethylenedioxy)indolin-2-one 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 15-冠醚-5 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.5h， 生成 (2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(5-bromo-7-methyl-2-oxospiro[indoline-3,2'-[1,3]dioxan]-1-yl)tetrahydro-2H-pyran-3,4-diyl diacetate 、 (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-((5-bromo-7-methylspiro[indole-3,2'-[1,3]dioxan]-2-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Synthesis of heteroaromatic N-β-glycosides of N-acetylglucosamine under phase transfer conditions: II. Indolin-2-one glycosaminides

  摘要：

  Regioselective N-beta-glucosamination of various unsubstituted or C4-, C5-, or C6-monosubstituted indolin-2-ones under phase transfer conditions was studied. The regioselectivity was unambiguously proved by H-1 NMR spectroscopy and X-ray analysis. The presence of substituent at C7 of the aromatic ring leads to the formation of either a mixture of isomeric N-beta- and O-beta-D-glucosaminides, or only oxazoline and/or 2-acetamidoglycal irrespective of the reaction conditions.

  DOI：

  10.1134/s1068162008060137