2-O-benzyl-1-O-(o-methoxybenzyl)-D-erythritol | 1310460-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-benzyl-1-O-(o-methoxybenzyl)-D-erythritol
• 英文别名: 2-O-benzyl-1-O-(p-methoxybenzyl)-D-erythritol
• CAS: 1310460-71-9
• 化学式: C₁₉H₂₄O₅
• 分子量: 332.397
• InChiKey: WZPHACSMQPBWCG-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-O-benzyl-1-O-(o-methoxybenzyl)-D-erythritol 在 三苯基膦 、 tetrafluoroboric acid dimethyl ether complex 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 1,4-dideoxy-1,4-[(R)-[2-O-benzyl-4-deoxy-D-erythritol-4-yl]episulfoniumylidene]-D-arabitol tetrafluoroborate
  参考文献：
  名称：

  Biological evaluation of 3′-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3′ position in the side chain on the α-glucosidase inhibitory activity

  摘要：

  Four analogs with 3'-O-alkyl groups (9a: CH(3), 9b: C(2)H(5), 9c: C(13)H(27) or 9d: CH(2)Ph) instead of the 3'-O-sulfate anion in salacinol (1), a naturally occurring potent alpha-glucosidase inhibitor, were synthesized by the coupling reaction of 1,4-dideoxy-1,4-epithio-D-arabinitols (18a and 18b) with appropriate epoxides (10a-10d). These analogs showed equal or considerably higher inhibitory activity against rat small intestinal alpha-glucosidases than the original sulfate (1), and one of them (9d) was found more potent than currently used alpha-glucosidase inhibitors as antidiabetics. Thus, introduction of a hydrophobic moiety at the C3' position of this new class of inhibitor was found beneficial for onset of stronger inhibition against these enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.109
• 作为产物：
  描述：

  溴甲苯 在 水 、 sodium hydride 、 二正丁基氧化锡 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 2-O-benzyl-1-O-(o-methoxybenzyl)-D-erythritol
  参考文献：
  名称：

  Biological evaluation of 3′-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3′ position in the side chain on the α-glucosidase inhibitory activity

  摘要：

  Four analogs with 3'-O-alkyl groups (9a: CH(3), 9b: C(2)H(5), 9c: C(13)H(27) or 9d: CH(2)Ph) instead of the 3'-O-sulfate anion in salacinol (1), a naturally occurring potent alpha-glucosidase inhibitor, were synthesized by the coupling reaction of 1,4-dideoxy-1,4-epithio-D-arabinitols (18a and 18b) with appropriate epoxides (10a-10d). These analogs showed equal or considerably higher inhibitory activity against rat small intestinal alpha-glucosidases than the original sulfate (1), and one of them (9d) was found more potent than currently used alpha-glucosidase inhibitors as antidiabetics. Thus, introduction of a hydrophobic moiety at the C3' position of this new class of inhibitor was found beneficial for onset of stronger inhibition against these enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.109

文献信息

• EP2671879
  申请人：——

  公开号：——

  公开（公告）日：——