6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-tagatose | 1314231-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-tagatose
• 英文别名: (3'aS,4R,6'R,6'aS)-6'-(azidomethyl)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]
• CAS: 1314231-75-8
• 化学式: C₁₂H₁₉N₃O₅
• 分子量: 285.3
• InChiKey: KITAXHMPMRGMJJ-JDVQERKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-tagatose 在 Dowex resin 50W X₈ H⁺ 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 生成 6-azido-6-deoxy-D-tagatose 、 6-azido-6-deoxy-D-tagatose
  参考文献：
  名称：

  Looking-Glass Synergistic Pharmacological Chaperones: DGJ and L-DGJ from the Enantiomers of Tagatose

  摘要：

  The enantiomers of tagatose are converted to L-DGJ [a noncompetitive inhibitor of human lysosome alpha-galactosidase A (alpha-Gal A), K-i 38.5 mu M] and DGJ [a competitive inhibitor of alpha-Gal A, K-i 15.1 nM] in 66% yield. L-DGJ and DGJ provide the first examples of pharmacological chaperones that (a) are enantiomeric iminosugars and (b) have synergistic activity with implications for the treatment of lysosomal storage disorders and other protein deficiencies.

  DOI：

  10.1021/ol201552q
• 作为产物：
  描述：

  乳果糖杂质 在 吡啶 、 sodium azide 、 copper(II) sulfate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-tagatose
  参考文献：
  名称：

  Looking-Glass Synergistic Pharmacological Chaperones: DGJ and L-DGJ from the Enantiomers of Tagatose

  摘要：

  The enantiomers of tagatose are converted to L-DGJ [a noncompetitive inhibitor of human lysosome alpha-galactosidase A (alpha-Gal A), K-i 38.5 mu M] and DGJ [a competitive inhibitor of alpha-Gal A, K-i 15.1 nM] in 66% yield. L-DGJ and DGJ provide the first examples of pharmacological chaperones that (a) are enantiomeric iminosugars and (b) have synergistic activity with implications for the treatment of lysosomal storage disorders and other protein deficiencies.

  DOI：

  10.1021/ol201552q

文献信息

• Looking-Glass Synergistic Pharmacological Chaperones: DGJ and L-DGJ from the Enantiomers of Tagatose
  作者：Sarah F. Jenkinson、George W. J. Fleet、Robert J. Nash、Yuriko Koike、Isao Adachi、Akihide Yoshihara、Kenji Morimoto、Ken Izumori、Atsushi Kato

  DOI：10.1021/ol201552q

  日期：2011.8.5

  The enantiomers of tagatose are converted to L-DGJ [a noncompetitive inhibitor of human lysosome alpha-galactosidase A (alpha-Gal A), K-i 38.5 mu M] and DGJ [a competitive inhibitor of alpha-Gal A, K-i 15.1 nM] in 66% yield. L-DGJ and DGJ provide the first examples of pharmacological chaperones that (a) are enantiomeric iminosugars and (b) have synergistic activity with implications for the treatment of lysosomal storage disorders and other protein deficiencies.