methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1-3)-2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside | 304866-17-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1-3)-2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5S,6S)-6-[[(4aR,6R,7R,8R,8aS)-7-amino-6-methoxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3,4-diacetyloxy-5-azidooxan-2-yl]methyl acetate
• CAS: 304866-17-9
• 化学式: C₂₂H₃₄N₄O₁₂
• 分子量: 546.532
• InChiKey: UTMXNBIUGZQZEU-ZESVGKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1-3)-2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 、 乙酸酐 在 吡啶 作用下， 反应 18.0h， 以100%的产率得到methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1-3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
  参考文献：
  名称：

  The Mild Cleavage of 2-Amino-2-deoxy-d-glucoside Methoxycarbonyl Derivatives

  摘要：

  [GRAPHICS]The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl3 and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl3 in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.

  DOI：

  10.1021/ol0063353
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonyl-amino-α-D-glucopyranosyl trichloroacetimidate 在 silver trifluoromethanesulfonate 、 sodium 、 对甲苯磺酸 甲基三氯硅烷 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 水 、 氢溴酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 111.0h， 生成 methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1-3)-2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
  参考文献：
  名称：

  The Mild Cleavage of 2-Amino-2-deoxy-d-glucoside Methoxycarbonyl Derivatives

  摘要：

  [GRAPHICS]The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl3 and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl3 in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.

  DOI：

  10.1021/ol0063353