5-amino-1,5,6-trideoxy-D-allose | 158705-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-amino-1,5,6-trideoxy-D-allose
• 英文别名: (2R,3R,4S,5S)-2-methylpiperidine-3,4,5-triol
• CAS: 158705-81-8
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: VYOCYWDJTQRZLC-MOJAZDJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-amino-1,5,6-trideoxy-D-allose 以 吡啶 为溶剂， 反应 48.0h， 以35%的产率得到
  参考文献：
  名称：

  1,6- Dideoxynojirimycin的合成1,6-二脱氧D-同种异体-nojirimycin，和1,6-二脱氧D-庚-nojirimycin通过不对称杂狄尔斯-阿尔德反应

  摘要：

  不对称狄尔斯-阿尔德反应而山梨醛ö甲基肟1D与手性chloronitroso衍生物2 d甘露糖，接着由主环加成的锇酸酯化，导致二醇6A具有优异的对映选择性（ee值> 99％;方案1）。的催化氢解6A得到1,6-二脱氧D-同种异体-nojirimycin（图7a）。环状硫酸盐8的亲核开环允许直接合成1,6-二脱氧野oji霉素（11）和1,6-二脱氧-D-古洛基-野oji霉素（12；方案2）。

  DOI：

  10.1002/hlca.19960790223
• 作为产物：
  描述：

  sorbaldehyde dimethylacetal 在 palladium on activated charcoal barium dihydroxide 、 四氧化锇 、 N-甲基吲哚酮 、 甲酸甲酯 、 1-deoxy-2,3:5,6-di-O-isopropylidene-1-nitroso-α-D-mannofutanosyl chloride 、 二氧化硫 、 氢气 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 252.0h， 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

文献信息

• De novo asymmetric synthesis of two 5-amino-5,6-dideoxy-D-allose derivatives
  作者：Albert Defoin、Hervé Sarazin、Christiane Strehler、Jacques Streith

  DOI：10.1016/s0040-4039(00)77271-6

  日期：1994.8

  cycloaddition of sorbic aldehyde derivative 9 and of sorbic acid 10 with the chiral chloro-nitroso dienophile 7 led with excellent regio- and diastereoselectivity to the chiral cycloadducts 11a and 12, respectively. Catalytic osmylation of their Bzl-derivatives 11b and 13b, followed by reductive cleavage of the NO bonds, gave ultimately the chiral aminoallose derivatives D-5 and D-6 which are potential

  山梨酸醛的狄尔斯-阿尔德环加成衍生物9和山梨酸10与手性氯亚硝基亲双烯体7导致具有优异的区域选择性和非对映选择性的手性cycloadducts 11A和12分别。它们的Bzl衍生物11b和13b的催化同化作用，然后NO键的还原性切割，最终得到了手性氨基阿糖衍生物D-5和D-6，它们是潜在的糖苷酶抑制剂。
• Synthesis of 1,6-Dideoxynojirimycin, 1,6-Dideoxy-D-allo-nojirimycin, and 1,6-Dideoxy-D-gulo-nojirimycinvia Asymmetric Hetero-Diels-Alder Reactions
  作者：Albert Defoin、Herv� Sarazin、Jacques Streith

  DOI：10.1002/hlca.19960790223

  日期：1996.3.20

  Asymmetric Diels-Alder reaction of sorbaldehyde O-methyloxime 1d with chiral chloronitroso derivative 2 of D-mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%; Scheme 1). Catalytic hydrogenolysis of 6a gave 1,6-dideoxy-D-allo-nojirimycin (7a). Nucleophilic ring opening of cyclic sulfate 8 allowed a straightforward synthesis of 1,

  不对称狄尔斯-阿尔德反应而山梨醛ö甲基肟1D与手性chloronitroso衍生物2 d甘露糖，接着由主环加成的锇酸酯化，导致二醇6A具有优异的对映选择性（ee值> 99％;方案1）。的催化氢解6A得到1,6-二脱氧D-同种异体-nojirimycin（图7a）。环状硫酸盐8的亲核开环允许直接合成1,6-二脱氧野oji霉素（11）和1,6-二脱氧-D-古洛基-野oji霉素（12；方案2）。
• 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.