5S-amino-1R,2S,3S,4S-cyclohexanetetrol | 108589-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5S-amino-1R,2S,3S,4S-cyclohexanetetrol
• 英文别名: 3-amino-2,3-dideoxy-D-epi-inositol；(1R,2S,3S,4S,5S)-5-aminocyclohexane-1,2,3,4-tetrol
• CAS: 108589-73-7
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: QXQNRSUOYNMXDL-GNFDWLABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  107
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  原栎醇 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 15-冠醚-5 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5S-amino-1R,2S,3S,4S-cyclohexanetetrol
  参考文献：
  名称：

  N-Arylmethylaminoquercitols, a new series of effective antidiabetic agents having α-glucosidase inhibition and antioxidant activity

  摘要：

  A new series of N-arylalkylaminoquercitols were synthesized by reductive amination of aminoquercitol bisacetonide 5 and a variety of aryl aldehydes. The targeted N-substituted aminoquercitols having phenolic moiety (7a-7c) displayed significantly enhanced alpha-glucosidase inhibition, which is 26-32 times more potent than that of the unmodified aminoquercitol 6. In addition, compounds 7a-7c also retained antioxidant activity with relatively more pronounced potency than their original phenolics. This recent finding suggests an approach to develop effective antidiabetic agents by incorporating antioxidative moiety into aminocyclitol core structure. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.033

文献信息

• (+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols
  作者：Sumrit Wacharasindhu、Wisuttaya Worawalai、Wimolpun Rungprom、Preecha Phuwapraisirisan

  DOI：10.1016/j.tetlet.2009.02.153

  日期：2009.5

  diastereomerically pure 5-amino-1,2,3,4-cyclohexanetetrols (6 and 11) and quercitol derivatives from naturally available (+)-proto-quercitol (1) is described. The stereochemistry of 1 is perfectly set up for regioselective protection of the hydroxy group which was further functionalized into the target aminocyclitol in a straightforward manner. The present approach provides a protocol for preparing aminocyclitols

  描述了由天然可得的（+）-原-槲皮醇（1）有效合成非对映体纯的5-氨基-1,2,3,4-环己烷四醇（6和11）和槲皮醇衍生物。立体化学1的建立是为了对羟基进行区域选择性保护，该羟基以直接的方式进一步官能化成目标氨基环糖醇。本方法提供了用于大量制备氨基环醇的方案。另外，使用改进的Mosher方法解决了（+）-原-槲皮醇的绝对立体化学。在合成的氨基环糖醇中，有11种可能通过IC抑制α-葡萄糖苷酶50值12.5μM，其比标准降糖药，阿卡波糖的大45倍的®。
• Chemical synthesis of 3-amino-2,3-dideoxy-d-myo-inositol (an intermediate in the biosynthesis of 2-deoxystreptamine) and its d-epi stereoisomer
  作者：Hans H. Baer、Lisa Siemsen、David J. Astles

  DOI：10.1016/s0008-6215(00)90119-8

  日期：1986.11
• N-Arylmethylaminoquercitols, a new series of effective antidiabetic agents having α-glucosidase inhibition and antioxidant activity
  作者：Wisuttaya Worawalai、Sumrit Wacharasindhu、Preecha Phuwapraisirisan

  DOI：10.1016/j.bmcl.2015.04.033

  日期：2015.6

  A new series of N-arylalkylaminoquercitols were synthesized by reductive amination of aminoquercitol bisacetonide 5 and a variety of aryl aldehydes. The targeted N-substituted aminoquercitols having phenolic moiety (7a-7c) displayed significantly enhanced alpha-glucosidase inhibition, which is 26-32 times more potent than that of the unmodified aminoquercitol 6. In addition, compounds 7a-7c also retained antioxidant activity with relatively more pronounced potency than their original phenolics. This recent finding suggests an approach to develop effective antidiabetic agents by incorporating antioxidative moiety into aminocyclitol core structure. (C) 2015 Elsevier Ltd. All rights reserved.