6-azido-3,4-di-O-benzyl-2-C-benzyloxymethyl-2,6-dideoxy-D-gluco-δ-lactam | 682771-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 6-azido-3,4-di-O-benzyl-2-C-benzyloxymethyl-2,6-dideoxy-D-gluco-δ-lactam
• CAS: 682771-62-6
• 化学式: C₂₈H₃₀N₄O₄
• 分子量: 486.571
• InChiKey: MHYSYIVMDROCDX-FPCALVHFSA-N

反应信息

• 作为反应物：
  描述：

  6-azido-3,4-di-O-benzyl-2-C-benzyloxymethyl-2,6-dideoxy-D-gluco-δ-lactam 在 palladium on activated charcoal 水 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 N-((2R,3R,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-6-oxo-piperidin-2-ylmethyl)-acetamide
  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-gluco-δ-lactam 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 6-azido-3,4-di-O-benzyl-2-C-benzyloxymethyl-2,6-dideoxy-D-gluco-δ-lactam
  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