methyl 3-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-hydroxytetrahydro-2H-pyran-2-yl)propanoate | 1226983-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-hydroxytetrahydro-2H-pyran-2-yl)propanoate
• 英文别名: methyl 3-[(2S,3R,4S,5R,6R)-2-hydroxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propanoate
• CAS: 1226983-41-0
• 化学式: C₃₈H₄₂O₈
• 分子量: 626.747
• InChiKey: ZNGZDIOZDWJUFI-KFHNNOKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-hydroxytetrahydro-2H-pyran-2-yl)propanoate 在 叠氮基三甲基硅烷 、 碘 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到methyl 3-((2S,3R,4S,5R,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)propanoate
  参考文献：
  名称：

  Molecular iodine-promoted N- and C-glycosylation of 1-C-alkyl (or phenyl)-glycopyranoses

  摘要：

  Molecular iodine efficiently promoted the N- and C-glycosylation of hemiketals with Me3SiN3 and Me3SiCN, respectively. Using this method we have prepared diverse functional N- and C-ketosides, which could serve as useful synthons for the preparation of unnatural glycosyl amino acids or glycopeptides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.124
• 作为产物：
  描述：

  methyl 3-[(3R,4S,5R,6R)-2-nitro-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propanoate 在 silica gel 作用下， 生成 methyl 3-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-hydroxytetrahydro-2H-pyran-2-yl)propanoate
  参考文献：
  名称：

  异头硝基糖的叠氮化：作为螺糖苷酶抑制剂在螺氨基化合物合成中的应用

  摘要：

  由叠氮基酯合成了6,5-融合糖衍生的螺氨基化合物，叠氮基酯是通过衍生自1-硝基糖的不稳定Michael加合物的亲核取代反应获得的。合成的大多数螺氨基苯胺对某些糖苷酶显示出中等但选择性的抑制活性。

  DOI：

  10.1016/j.tetlet.2010.03.003

文献信息

• Molecular iodine-promoted N- and C-glycosylation of 1-C-alkyl (or phenyl)-glycopyranoses
  作者：A.P. John Pal、Asadulla Mallick、Y. Suman Reddy、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2010.09.124

  日期：2010.12

  Molecular iodine efficiently promoted the N- and C-glycosylation of hemiketals with Me3SiN3 and Me3SiCN, respectively. Using this method we have prepared diverse functional N- and C-ketosides, which could serve as useful synthons for the preparation of unnatural glycosyl amino acids or glycopeptides. (C) 2010 Elsevier Ltd. All rights reserved.
• Azidation of anomeric nitro sugars: application in the synthesis of spiroaminals as glycosidase inhibitors
  作者：A.P. John Pal、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2010.03.003

  日期：2010.5

  been synthesized from the azido esters obtained via the nucleophilic substitution reactions of unstable Michael adducts derived from 1-nitro sugars. Most of the spiroaminals synthesized showed moderate but selective inhibitory activities toward some glycosidases.

  由叠氮基酯合成了6,5-融合糖衍生的螺氨基化合物，叠氮基酯是通过衍生自1-硝基糖的不稳定Michael加合物的亲核取代反应获得的。合成的大多数螺氨基苯胺对某些糖苷酶显示出中等但选择性的抑制活性。