6-amino-6-deoxy-D-galactonic acid | 906066-50-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 6-amino-6-deoxy-D-galactonic acid
• 英文别名: 6-amino-galactonic acid；ε-Amino-α.β.γ.δ-tetraoxy-n-capronsaeure；6-Amino-galaktonsaeure；5-Amino-1.2.3.4-tetraoxy-pentan-carbonsaeure-(1)；(2R,3S,4S,5R)-6-amino-2,3,4,5-tetrahydroxyhexanoic acid
• CAS: 906066-50-0
• 化学式: C₆H₁₃NO₆
• 分子量: 195.172
• InChiKey: CTWCTXWYMCZWOK-MGCNEYSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  144
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-azido-6-deoxy-D-galactono-1,4-lactone 在 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium tetrahydroborate 、 氢气 、 potassium bromide 作用下， 以 乙醇 、 水 为溶剂， 反应 99.0h， 生成 6-amino-6-deoxy-D-galactonic acid
  参考文献：
  名称：

  The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6

  摘要：

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.018

文献信息

• Freudenberg; Doser, Chemische Berichte, 1925, vol. 58, p. 294,296
  作者：Freudenberg、Doser

  DOI：——

  日期：——
• The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
  作者：Ludovic Chaveriat、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/j.tetasy.2006.04.018

  日期：2006.5

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.