benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside | 95066-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside
• 英文别名: benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-D-mannopyranoside；Benzyl-4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside；[(3aS,4S,6S,7R,7aS)-7-amino-2,2-dimethyl-4-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]methanol
• CAS: 95066-29-8
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: GVAVEERTOPOCPH-MRLBHPIUSA-N

物化性质

• 沸点：
  445.6±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside 在 钯 3 A molecular sieve 、 氢气 、 碳酸氢钠 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 重水 、 溶剂黄146 为溶剂， 反应 189.0h， 生成 八倾吲嗪三醇
  参考文献：
  名称：

  Synthesis of the α-Mannosidase inhibitors swainsonine [(1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine] and 1,4-dideoxy-1,4-imino-d-mannitol from mannose

  摘要：

  DOI：

  10.1016/s0040-4020(01)86850-2
• 作为产物：
  描述：

  D-甘露糖 在 钯 吡啶 、 咪唑 、 sodium tetrahydroborate 、 sodium azide 、 3 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 乙酰氯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 79.5h， 生成 benzyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of the α-Mannosidase inhibitors swainsonine [(1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine] and 1,4-dideoxy-1,4-imino-d-mannitol from mannose

  摘要：

  DOI：

  10.1016/s0040-4020(01)86850-2

文献信息

• 3, 5, and/or 6 substituted analogues of swainsonine processes for their
  申请人：GlycoDesign

  公开号：US06048870A1

  公开（公告）日：2000-04-11

  The invention relates to novel 3, 5, and/or 6 swainsonine analogues, processes for their preparation and their use as therapeutic agents. The invention also relates to pharmaceutical compositions containing the compounds and their use as therapeutics.

  本发明涉及新型3、5和/或6 swainsonine类似物，其制备过程及其作为治疗剂的使用。本发明还涉及含有该化合物的药物组合物及其作为治疗剂的使用。
• Design synthesis and preliminary evaluation of a potent α- mannosidase inhibitor: 1,4-dideoxy-1,4-imino-<scp>D</scp>-mannitol
  作者：George W. J. Fleet、Paul W. Smith、Stephen V. Evans、Linda E. Fellows

  DOI：10.1039/c39840001240

  日期：——

  1,4-Dideoxy-1,4-imino-D-mannitol (1), synthesised from benzyl α-D-mannopyranoside, is a potent competitive inhibitor of the hydrolysis of p-nitrophenyl α-D-mannopyranoside catalysed by Jack Bean α-mannosidase (Cnavalia ensiformis); this is the first report of the specific inhibition of a glycosidase by a pyrrolidine analogue of a furanose sugar.

  1,4-二脱氧-1,4-亚氨基d -mannitol（1）中，从合成的苄基α- d -mannopyranoside，是水解的有效竞争性抑制剂p硝基苯基α- d -mannopyranoside由刀豆α催化的-甘露糖苷酶（Cnavalia ensiformis）；这是呋喃糖的吡咯烷类似物特异性抑制糖苷酶的首次报道。
• Novel 3,5,and/or 6 substituted analogues of swainsonine processes for their preparation and their use as therapeutic agents
  申请人：GlycoDesign Inc.

  公开号：US20030236229A1

  公开（公告）日：2003-12-25

  The invention relates to novel 3, 5, and/or 6 swainsoninc analogues, processes for their preparation and their use as therapeutic agents. The invention also relates to pharmaceutical compositions containing the compounds and their use as therapeutics.

  本发明涉及新型3、5和/或6 swainsoninc类似物，其制备过程以及它们作为治疗剂的用途。本发明还涉及含有这些化合物的药物组合物以及它们作为治疗剂的用途。
• Novel 3, 5, and/or 6 substituted analogues of swainsonine, processes for their preparation and their use as therapeutic agents
  申请人：GlycoDesign Inc.

  公开号：US20020099065A1

  公开（公告）日：2002-07-25

  The invention related to novel 3, 5, and/or 6 swainsonine analogues, processes for their preparation and their use as therapeutic agents. The invention also relates to pharmaceutical compositions containing the compounds and their use as therapeutics.

  本发明涉及新型的3、5和/或6 swainsonine类似物，以及它们的制备方法和它们作为治疗剂的用途。本发明还涉及包含这些化合物的药物组合物和它们作为治疗剂的用途。
• Pyrrolidine and hexahydro-1 H-azepine mimics of the ‘flap up’ mannosyl cation
  作者：Robert A. Farr、Amy K. Holland、Edward W. Huber、Norton P. Peet、Philip M. Weintraub

  DOI：10.1016/s0040-4020(01)80815-2

  日期：1994.1

  The pyrrolidine 4, 6-amino-1,4,6-trideoxy-1,4-imino-D-mannitol dihydrochloride, and the hexahydro-1H-azepine 5, 4-amino-1,4,6-trideoxy-1,6-imino-D-mannitol dihydrochloride, were synthesized as potential inhibitors of alpha-mannosidase.