methyl 3,4,6-tri-O-acethyl-2-amino-2-deoxy-β-D-glucopyranosyl-(1-6)-2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranoside | 304866-09-9

• 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-acethyl-2-amino-2-deoxy-β-D-glucopyranosyl-(1-6)-2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranoside
• 英文别名: GlcN3Ac4Ac6Ac(b1-6)[Bn(-2)][Bn(-3)][Mob(-4)]b-Glc1Me；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-[[(2R,3R,4S,5R,6R)-6-methoxy-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 304866-09-9
• 化学式: C₄₁H₅₁NO₁₄
• 分子量: 781.854
• InChiKey: QOPFFLINBKTUJQ-UEQIGFESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  56
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 3,4,6-tri-O-acethyl-2-amino-2-deoxy-β-D-glucopyranosyl-(1-6)-2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1-6)-2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-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 甲基三氯硅烷 、 4 A molecular sieve 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 methyl 3,4,6-tri-O-acethyl-2-amino-2-deoxy-β-D-glucopyranosyl-(1-6)-2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-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