(2R,3R,4R,5R)-5-amino-1,1-dimethoxyhexane-2,3,4-triol | 197294-89-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3R,4R,5R)-5-amino-1,1-dimethoxyhexane-2,3,4-triol
• CAS: 197294-89-6
• 化学式: C₈H₁₉NO₅
• 分子量: 209.243
• InChiKey: UGFPOSOJCOQMDH-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-5-amino-1,1-dimethoxyhexane-2,3,4-triol 在 palladium on activated charcoal barium dihydroxide 、 二氧化硫 、 氢气 作用下， 以 水 为溶剂， 反应 105.0h， 生成 5-amino-1,5,6-trideoxy-D-allose
  参考文献：
  名称：

  6-Deoxy-allo-nojirimycin in the racemic and d-series, 6-deoxy-d,l-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-d,l-allosamine via hetero-Diels-Alder cycloadditions

  摘要：

  Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cycloadducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6-deoxy-2-D,L-allosamine 15b, to 6-deoxy-D,L and D-allo-nojirimycin 15a, D-15a, to 6-deoxy-D,L-talo-nojirimycin 15c as well as to their l-deoxy-derivatives 16a, D-16a, 16c via their crystalline l-deoxy-l-sulfonic acid derivatives (sulfite adducts). Amino-sugars 16a,c are mixtures of alpha- and -beta-anomers and of the corresponding imines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00897-1
• 作为产物：
  描述：

  sorbaldehyde dimethylacetal 在 palladium on activated charcoal 四氧化锇 、 N-甲基吲哚酮 、 氢气 作用下， 反应 24.0h， 生成 (2R,3R,4R,5R)-5-amino-1,1-dimethoxyhexane-2,3,4-triol
  参考文献：
  名称：

  6-Deoxy-allo-nojirimycin in the racemic and d-series, 6-deoxy-d,l-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-d,l-allosamine via hetero-Diels-Alder cycloadditions

  摘要：

  Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cycloadducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6-deoxy-2-D,L-allosamine 15b, to 6-deoxy-D,L and D-allo-nojirimycin 15a, D-15a, to 6-deoxy-D,L-talo-nojirimycin 15c as well as to their l-deoxy-derivatives 16a, D-16a, 16c via their crystalline l-deoxy-l-sulfonic acid derivatives (sulfite adducts). Amino-sugars 16a,c are mixtures of alpha- and -beta-anomers and of the corresponding imines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00897-1

文献信息

• Total syntheses of (±) aminoallose derivatives
  作者：Albert Defoin、Hans Fritz、Guillaume Geffroy、Jacques Streith

  DOI：10.1016/s0040-4039(00)85049-2

  日期：1986.1
• A straightforward synthesis of (±) 5-amino-5,6-dideoxyallose, of its bisulfite β-anomer, and of its 1-deoxy derivative
  作者：Albert Defoin、Hervé Sarazin、Jacques Streith

  DOI：10.1016/s0040-4039(00)79341-5

  日期：1993.7

  Diels-Alder cycloaddition of (E,E)-hexadienal dimethylacetal 3 with the benzyloxycarbonylnitroso dienophile 4, followed by catalytic osmylation, hydrogenolysis, and treatment with SO2, led stereospecifically to the sole beta-anomer of allopiperidinose bisulfite derivative 7. Saponification of 7 and thence catalytic hydrogenation gave in high yield the 1-deoxyallopiperidine derivative 9.
• 6-Deoxy-allo-nojirimycin in the racemic and d-series, 6-deoxy-d,l-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-d,l-allosamine via hetero-Diels-Alder cycloadditions
  作者：Albert Defoin、Hervé Sarazin、Jacques Streith

  DOI：10.1016/s0040-4020(97)00897-1

  日期：1997.10

  Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cycloadducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6-deoxy-2-D,L-allosamine 15b, to 6-deoxy-D,L and D-allo-nojirimycin 15a, D-15a, to 6-deoxy-D,L-talo-nojirimycin 15c as well as to their l-deoxy-derivatives 16a, D-16a, 16c via their crystalline l-deoxy-l-sulfonic acid derivatives (sulfite adducts). Amino-sugars 16a,c are mixtures of alpha- and -beta-anomers and of the corresponding imines. (C) 1997 Elsevier Science Ltd.