3,4-di-O-benzyl-2-C-benzyloxymethyl-6-O-tert-butyldimethylsilyl-2-deoxy-D-gluco-δ-lactam | 682771-59-1

• 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: 3,4-di-O-benzyl-2-C-benzyloxymethyl-6-O-tert-butyldimethylsilyl-2-deoxy-D-gluco-δ-lactam
• CAS: 682771-59-1
• 化学式: C₃₄H₄₅NO₅Si
• 分子量: 575.821
• InChiKey: LBPZPBVLTWGSGO-SEVDZJIVSA-N

物化性质

• 沸点：
  654.6±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzyl-2-C-benzyloxymethyl-6-O-tert-butyldimethylsilyl-2-deoxy-D-gluco-δ-lactam 在 palladium on activated charcoal 吡啶 、 sodium azide 、 四丁基氟化铵 、 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 44.75h， 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：

  (3R,4R,5S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-piperidin-2-one 在 甲酸 、 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以63%的产率得到3,4-di-O-benzyl-2-C-benzyloxymethyl-6-O-tert-butyldimethylsilyl-2-deoxy-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