((3aS,5S,6R,6aS)-6-Benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-butyl-amine | 858675-55-5

• 分子结构分类: 有机化合物
• 英文名称: ((3aS,5S,6R,6aS)-6-Benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-butyl-amine
• CAS: 858675-55-5
• 化学式: C₂₇H₃₇NO₅
• 分子量: 455.594
• InChiKey: VOZINZVEOCQHLL-SFIUMABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.18
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((3aS,5S,6R,6aS)-6-Benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-butyl-amine 在 palladium on activated charcoal 盐酸 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 148.0h， 生成 N-butyl-4-O-butyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  Design and synthesis of iminosugar-based inhibitors of glucosylceramide synthase: the search for new therapeutic agents against Gaucher disease

  摘要：

  A series Of iminosugars bearing two or three alkyl chains ('iminoglycolipids') were designed as ceramide mimics and analogues of N-butyl 1-deoxynojirimycin (N-Bu DNJ, Zavesca(R)). This orally active iminosugar inhibits the biosynthesis of glucosylceramides. which accumulate pathologically in macrophages of patients with Gaucher disease (substrate reduction therapy, SRT). Molecular modeling and kinetic experiments have suggested that N-Bu DNJ is a competitive inhibitor that mimics the ceramide acceptor but not the donor substrate (UDP-glucose) in the glucosylceramide synthase-catalyzed process. Kinetic measurements were made with the glucosyltransferase to assess the selectivity of the new iminoglycolipids with respect to the length (C-4 or C-8) and the position of the second alkyl chain (C-1, O-2 and/or O-4). This structure-activity relationship study showed that the addition of a second alkyl chain, to obtain better ceramide mimics, led to less potent inhibitors. Moreover, the synthase active site did not discriminate inhibitors differing by the position of the second alkyl chain (C-1, O-2 or O-4). Best inhibition Was found for 1,5-dideoxy-1.5-iimino-N-octyl-4-O-octyl-D-glucitol (IC50 134 mu M). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.015
• 作为产物：
  描述：

  1,4-di-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 ((3aS,5S,6R,6aS)-6-Benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-butyl-amine
  参考文献：
  名称：

  Design and synthesis of iminosugar-based inhibitors of glucosylceramide synthase: the search for new therapeutic agents against Gaucher disease

  摘要：

  A series Of iminosugars bearing two or three alkyl chains ('iminoglycolipids') were designed as ceramide mimics and analogues of N-butyl 1-deoxynojirimycin (N-Bu DNJ, Zavesca(R)). This orally active iminosugar inhibits the biosynthesis of glucosylceramides. which accumulate pathologically in macrophages of patients with Gaucher disease (substrate reduction therapy, SRT). Molecular modeling and kinetic experiments have suggested that N-Bu DNJ is a competitive inhibitor that mimics the ceramide acceptor but not the donor substrate (UDP-glucose) in the glucosylceramide synthase-catalyzed process. Kinetic measurements were made with the glucosyltransferase to assess the selectivity of the new iminoglycolipids with respect to the length (C-4 or C-8) and the position of the second alkyl chain (C-1, O-2 and/or O-4). This structure-activity relationship study showed that the addition of a second alkyl chain, to obtain better ceramide mimics, led to less potent inhibitors. Moreover, the synthase active site did not discriminate inhibitors differing by the position of the second alkyl chain (C-1, O-2 or O-4). Best inhibition Was found for 1,5-dideoxy-1.5-iimino-N-octyl-4-O-octyl-D-glucitol (IC50 134 mu M). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.015