5-O-tert-butyldimethylsilyl-2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptitol | 934715-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-tert-butyldimethylsilyl-2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptitol
• CAS: 934715-97-6
• 化学式: C₂₃H₄₆O₇Si
• 分子量: 462.7
• InChiKey: WIEJKLFFNDMBSK-WPVAHCMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.61
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-O-tert-butyldimethylsilyl-2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptitol 在 吡啶 、 4-二甲氨基吡啶 、 溶剂黄146 、 三氟乙酸 作用下， 反应 77.5h， 生成 N-benzyl-1,4-imino-D-glycero-L-talo-heptitol
  参考文献：
  名称：

  Looking glass inhibitors: synthesis of a potent naringinase inhibitor l-DIM [1,4-dideoxy-1,4-imino-l-mannitol], the enantiomer of DIM [1,4-dideoxy-1,4-imino-d-mannitol] a potent α-d-mannosidase inhibitor

  摘要：

  The synthesis of L-DIM [1,4-dideoxy-1,4-imino-L-mannitol] and of 1,4-imino-D-glycero-L-talo-heptitol from D-glycero-D-gulyheptono-1,4-lactone depends on the use of pentan-3-one to form two five ring ketals as described by Burke, rather than the formation of one five ring and one six ring ketal formed with acetone. L-DIM, the enantiomer of the potent alpha-D-mannosidase inhibitor DIM [1,4-dideoxy-1,4-imino-D-mannitol] is a good inhibitor of naringinase (an alpha-L-rhatimosidase) with a K-i of 3.63 mu M. 1,4-Imino-D-glycero-L-talo-heptitol is a moderate inhibitor of naringinase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.010
• 作为产物：
  描述：

  在 咪唑 、 氢氧化钾 、 锂硼氢 、 Amberlyst 15 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.28h， 生成 5-O-tert-butyldimethylsilyl-2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptitol
  参考文献：
  名称：

  Looking glass inhibitors: synthesis of a potent naringinase inhibitor l-DIM [1,4-dideoxy-1,4-imino-l-mannitol], the enantiomer of DIM [1,4-dideoxy-1,4-imino-d-mannitol] a potent α-d-mannosidase inhibitor

  摘要：

  The synthesis of L-DIM [1,4-dideoxy-1,4-imino-L-mannitol] and of 1,4-imino-D-glycero-L-talo-heptitol from D-glycero-D-gulyheptono-1,4-lactone depends on the use of pentan-3-one to form two five ring ketals as described by Burke, rather than the formation of one five ring and one six ring ketal formed with acetone. L-DIM, the enantiomer of the potent alpha-D-mannosidase inhibitor DIM [1,4-dideoxy-1,4-imino-D-mannitol] is a good inhibitor of naringinase (an alpha-L-rhatimosidase) with a K-i of 3.63 mu M. 1,4-Imino-D-glycero-L-talo-heptitol is a moderate inhibitor of naringinase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.010