methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-deoxy-4,6-O-isoprpylidene-2-methoxycarbonylamino-β-D-glucopyranoside | 304865-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-deoxy-4,6-O-isoprpylidene-2-methoxycarbonylamino-β-D-glucopyranoside
• 英文别名: methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1-3)-2-deoxy-4,6-O-isopropylidene-2-methoxycarbonylamino-β-D-glucopyranoside；[(2R,3R,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-methoxy-7-(methoxycarbonylamino)-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 304865-98-3
• 化学式: C₂₆H₃₉NO₁₆
• 分子量: 621.593
• InChiKey: AJCQKSKRLASTDY-DWARJDMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  199
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-deoxy-4,6-O-isoprpylidene-2-methoxycarbonylamino-β-D-glucopyranoside 在 甲基三氯硅烷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成
  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-methoxycarbonylamino-α-D-glucopyranose 在 silver trifluoromethanesulfonate 、 sodium 、 对甲苯磺酸 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢溴酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 59.0h， 生成 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-deoxy-4,6-O-isoprpylidene-2-methoxycarbonylamino-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

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。