3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonyl-amino-α-D-glucopyranosyl trichloroacetimidate | 304865-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonyl-amino-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonylamino-α-D-glucopyranosyl trichloroacetimidate；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(methoxycarbonylamino)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 304865-93-8
• 化学式: C₁₆H₂₁Cl₃N₂O₁₀
• 分子量: 507.709
• InChiKey: GWCMCXZTYPQIJI-SYLRKERUSA-N

物化性质

• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonyl-amino-α-D-glucopyranosyl trichloroacetimidate 在 silver trifluoromethanesulfonate 甲基三氯硅烷 、 4 A molecular sieve 、 氢溴酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 61.0h， 生成 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-isocyanato-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：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-methoxycarbonylamino-α,β-D-glucopyranoside 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonyl-amino-α-D-glucopyranosyl trichloroacetimidate
  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

文献信息

• Gram-scale syntheses of the (1 → 3)-linked and (1 → 4)-linked hyaluronan disaccharides
  作者：Sara L. Adamski-Werner、Bryan K.S. Yeung、Lynne A. Miller-Deist、Peter A. Petillo

  DOI：10.1016/j.carres.2004.03.005

  日期：2004.5

  The first gram-scale syntheses of two hyaluronan disaccharides are described. Construction of the (1-->4)-linked disaccharide 12 was achieved in 12% overall yield using 2,3-bis-dimethyl acetal protection in combination with chlorosilane-induced carbamate cleavage methodologies. The uronic acid functionality was installed using TEMPO oxidation with NaOCl as the hypochlorite source. The (1-->3)-linked

  描述了两种透明质酸二糖的第一克级合成。（1-> 4）-连接的二糖12的构建使用2,3-双-二甲基乙缩醛保护结合氯硅烷诱导的氨基甲酸酯裂解方法以12％的总收率实现。使用TEMPO氧化并以NaOCl作为次氯酸盐源来安装糖醛酸官能团。除了使用氯硅烷诱导的氨基甲酸酯裂解方法和TEMPO氧化外，利用乙交酯保护剂还可以以7％的总收率获得（1-> 3）连接的二糖18。