2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptono-1,4-lactone | 929101-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptono-1,4-lactone
• 英文别名: 2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptano-1,4-lactone；(3aR,6R,6aR)-6-[(S)-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2,2-diethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 929101-58-6
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: IYNGBHGFVQNZHY-XVIXHAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptono-1,4-lactone 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 锂硼氢 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 142.5h， 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 氢氧化钾 、 Amberlyst 15 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.28h， 生成 2,3:6,7-di-O-diethylidene-D-glycero-L-talo-heptono-1,4-lactone
  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

文献信息

• Synthesis of the first example of a nucleoside analogue bearing a 5′-deoxy-β-d-allo-septanose as a seven-membered ring sugar moiety
  作者：Gwenaëlle Sizun、David Dukhan、Jean-François Griffon、Ludovic Griffe、Jean-Christophe Meillon、Frédéric Leroy、Richard Storer、Jean-Pierre Sommadossi、Gilles Gosselin

  DOI：10.1016/j.carres.2008.12.019

  日期：2009.3

  The first example of a nucleoside analogue bearing a 5'-deoxy-beta-D-allo-septanose as a seven-membered ring sugar moiety, namely 9-(5-deoxy-beta-D-allo-septanosyl)-adenine, is reported. This compound was synthesized in 14 steps from the commercially available D-glycero-D-gulo-1,4-lactone. When evaluated in cell culture experiments against a broad range of viruses, it did not exhibit any significant

  带有5'-脱氧-β-D-alal-septanose作为七元环糖部分，即9-（5-脱氧-β-D-allo-septanosyl）-腺嘌呤的核苷类似物的第一个例子是报告。该化合物由市售的D-甘油-D-gulo-1,4-内酯分14步合成。当在细胞培养实验中针对各种病毒进行评估时，它没有表现出任何显着的抗病毒作用或细胞毒性。