methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-β-D-gluco-6-enopyranoside | 1045825-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-β-D-gluco-6-enopyranoside
• CAS: 1045825-24-8
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: OPFJGHAEOANPIR-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-β-D-gluco-6-enopyranoside 在 正丁基锂 、 二氯二茂锆 、 臭氧 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.58h， 生成 (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-hydroxymethyl-2-(4-methoxybenzyloxy)-cyclopentanol 、 (1S,2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-hydroxymethyl-2-(4-methoxybenzyloxy)-cyclopentanol
  参考文献：
  名称：

  Synthetic studies towards a new scaffold, spirobicycloimidazoline

  摘要：

  A new scaffold consisting of a carbocycle and a substituted imidazoline in an orthogonal arrangement was synthesized as a potential specific inhibitor of glycosidases. The spirobicycloimidazoline, (5R,6R,7R,8R)-8-(hydroxymethyl)-2-phenyl-1,3-diazaspiro[4.4]non-1-ene-6,7-diol, was synthesized from methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-alpha/beta-D-gluco-6-enopyranoside via (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyloxy)-5-vinyl-cyclopentanol. The ring contraction of the 6-enopyranoside in the presence of zirconocene equivalent ('Cp2Zr') reagent gave exclusively the corresponding cyclopentanol without cleavage of the PMB protecting group. In the course of the study, a new alpha-mannosidase inhibitor, (1R,2R,3R,5R)-5-amino-3-hydroxymethyl-cyclopentane-1,2-diol, was also discovered. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.025
• 作为产物：
  描述：

  、 亚甲基三苯基膦烷 以 甲苯 为溶剂， 生成 methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-β-D-gluco-6-enopyranoside 、 methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-α-D-gluco-6-enopyranoside
  参考文献：
  名称：

  Synthetic studies towards a new scaffold, spirobicycloimidazoline

  摘要：

  A new scaffold consisting of a carbocycle and a substituted imidazoline in an orthogonal arrangement was synthesized as a potential specific inhibitor of glycosidases. The spirobicycloimidazoline, (5R,6R,7R,8R)-8-(hydroxymethyl)-2-phenyl-1,3-diazaspiro[4.4]non-1-ene-6,7-diol, was synthesized from methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-alpha/beta-D-gluco-6-enopyranoside via (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyloxy)-5-vinyl-cyclopentanol. The ring contraction of the 6-enopyranoside in the presence of zirconocene equivalent ('Cp2Zr') reagent gave exclusively the corresponding cyclopentanol without cleavage of the PMB protecting group. In the course of the study, a new alpha-mannosidase inhibitor, (1R,2R,3R,5R)-5-amino-3-hydroxymethyl-cyclopentane-1,2-diol, was also discovered. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.025