Methyl 4-amino-4-deoxy-α-D-mannopyranoside | 141232-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 4-amino-4-deoxy-α-D-mannopyranoside
• 英文别名: methyl 4-deoxy-4-amino-α-D-mannoside；(2S,3S,4S,5S,6S)-5-amino-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol
• CAS: 141232-03-3
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: LMHVHMYRVUPVRG-VEIUFWFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105.17
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Methyl 4-amino-4-deoxy-α-D-mannopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 Methyl 4-deoxy-4-<(1S)-(1,4/2,3,5)-2,3,4-trihydroxy-5-(hydroxymethyl)-2-cyclohexen-1-ylamino>-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and enzyme-inhibitory activity of methyl acarviosin analogues having the α- manno configuration

  摘要：

  Two methyl acarviosin analogues 3a and 4a, having the alpha-manno configuration, and their dihydro derivatives 6a and 7a were synthesised by coupling the protected pseudo-sugar epoxides with methyl 4-amino-4-deoxy- and -4,6-dideoxy-alpha-D-mannopyranoside. Similarly, two analogous compounds 5a and 8a composed of the 1,6-anhydro-beta-D-mannopyranose residues were prepared. Compound 7a showed mild inhibitory activity against Jack bean alpha-D-mannosidase, and 3a was a moderate inhibitor of both alpha-D-mannosidase and yeast alpha-D-glucosidase.

  DOI：

  10.1016/0008-6215(92)84056-x
• 作为产物：
  描述：

  Methyl 4-acetamido-2,3,6-tri-O-acetyl-4-deoxy-α-D-mannopyranoside 在 一水合肼 作用下， 反应 0.5h， 生成 Methyl 4-amino-4-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and enzyme-inhibitory activity of methyl acarviosin analogues having the α- manno configuration

  摘要：

  Two methyl acarviosin analogues 3a and 4a, having the alpha-manno configuration, and their dihydro derivatives 6a and 7a were synthesised by coupling the protected pseudo-sugar epoxides with methyl 4-amino-4-deoxy- and -4,6-dideoxy-alpha-D-mannopyranoside. Similarly, two analogous compounds 5a and 8a composed of the 1,6-anhydro-beta-D-mannopyranose residues were prepared. Compound 7a showed mild inhibitory activity against Jack bean alpha-D-mannosidase, and 3a was a moderate inhibitor of both alpha-D-mannosidase and yeast alpha-D-glucosidase.

  DOI：

  10.1016/0008-6215(92)84056-x

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
• Quantifying the Electronic Effects of Carbohydrate Hydroxy Groups by Using Aminosugar Models
  作者：Christian M. Pedersen、Jacob Olsen、Azra B. Brka、Mikael Bols

  DOI：10.1002/chem.201100020

  日期：2011.6.14

  their pKa values determined by titration. These model compounds were chosen because they are the amino derivatives of the most common glycosyl acceptors. From this study it was possible to evaluate the electron density at each of the given positions in the carbohydrate and compare them. Some general trends were observed: The basicity of the amino groups decreases in the order 6‐NH2>3‐NH2>2‐NH2>4‐NH2

  合成了具有α-和β-葡萄糖，α-半乳糖或α-甘露糖立体化学的甲基氨基脱氧糖苷，在四个可能的非异头位置中均具有氨基官能团，并通过滴定确定了其p K a值。选择这些模型化合物是因为它们是最常见的糖基受体的氨基衍生物。通过这项研究，有可能评估碳水化合物中每个给定位置的电子密度并进行比较。观察到一些一般趋势：氨基的碱度以6-NH 2 > 3-NH 2 > 2-NH 2 > 4-NH 2的顺序降低。（指的是位置）。当糖环上的一个或多个取代基为轴向时，氨基脱氧糖α的碱性通常会增加。当胺对氧原子为反平面时，碱度降低。这些发现与从糖基化化学和糖的区域选择性保护获得的观察结果一致。