(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-hexanoic acid amide | 682771-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-hexanoic acid amide
• CAS: 682771-57-9
• 化学式: C₃₄H₄₇NO₆Si
• 分子量: 593.836
• InChiKey: OLMDTGGSUMIULR-SEVDZJIVSA-N

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-hexanoic acid amide 在 乙酸酐 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 生成 (3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-piperidin-2-one 、 (3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-piperidin-2-one
  参考文献：
  名称：

  Design and synthesis of 2-acetamidomethyl derivatives of isofagomine as potential inhibitors of human lysosomal β-hexosaminidases

  摘要：

  As part of a program towards the development of specific inhibitors of human lysosomal beta-hexosaminidase for use as chemical chaperones in therapy of G(M2) gangliosidosis related diseases, the synthesis of 2-acetamidomethyl derivatives of isofagomine has been undertaken. Key event in this synthesis is the conversion of a C-2 substituted gluconolactone derivative into the corresponding lactam, followed by reduction to the corresponding amine. The 1-N-imino-2 acetamidomethyl derivative 5 proved to be a rather selective inhibitor with a K-i of 2.4 muM for homogenate of human spleen lysosomal beta-hexosaminidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.040
• 作为产物：
  描述：

  3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-D-glucose 在 咪唑 、 氨 、 乙酸酐 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-hexanoic acid amide
  参考文献：
  名称：

  Design and synthesis of 2-acetamidomethyl derivatives of isofagomine as potential inhibitors of human lysosomal β-hexosaminidases

  摘要：

  As part of a program towards the development of specific inhibitors of human lysosomal beta-hexosaminidase for use as chemical chaperones in therapy of G(M2) gangliosidosis related diseases, the synthesis of 2-acetamidomethyl derivatives of isofagomine has been undertaken. Key event in this synthesis is the conversion of a C-2 substituted gluconolactone derivative into the corresponding lactam, followed by reduction to the corresponding amine. The 1-N-imino-2 acetamidomethyl derivative 5 proved to be a rather selective inhibitor with a K-i of 2.4 muM for homogenate of human spleen lysosomal beta-hexosaminidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.040