(3aS,5R,6R,7S,7aS)-2-methyl-2-pent-4-enoxy-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran | 128503-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aS,5R,6R,7S,7aS)-2-methyl-2-pent-4-enoxy-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran
• CAS: 128503-36-6
• 化学式: C₃₄H₄₀O₇
• 分子量: 560.687
• InChiKey: XMQJUWHGYNRTFR-KLPHIQEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  41.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3aS,5R,6R,7S,7aS)-2-methyl-2-pent-4-enoxy-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran 在 三氟甲磺酸三甲基硅酯 、 硫酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 (2R,3R,4R,4aR,10bS)-8,10-dimethoxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromene
  参考文献：
  名称：

  Intramolecular C-glycosylation of 2-O-benzylated pentenyl mannopyranosides: remarkable 1,2-trans stereoselectivity

  摘要：

  The IDCP-promoted intramolecular C-glycosylation of pentenyl alpha-mannopyranosides carrying, at O-2, an activated benzyl group gave, unexpectedly, the 1,2-trans-fused bicyclic product which corresponds to an alpha-C-aryl mannopyranose derivative. This remarkable, strained C-glycosyl compound was rapidly epimerized to the more stable 1,2-cis product on treatment with BF3.Et2O. The IDCP-reaction product could be elaborated into a 2-(alpha-C-mannopyranosyl)-3,4,5-trimethoxybenzyl alcohol derivative. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.006
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 2,4,6-三甲基吡啶 为溶剂， 生成 (3aS,5R,6R,7S,7aS)-2-methyl-2-pent-4-enoxy-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran
  参考文献：
  名称：

  Intramolecular C-glycosylation of 2-O-benzylated pentenyl mannopyranosides: remarkable 1,2-trans stereoselectivity

  摘要：

  The IDCP-promoted intramolecular C-glycosylation of pentenyl alpha-mannopyranosides carrying, at O-2, an activated benzyl group gave, unexpectedly, the 1,2-trans-fused bicyclic product which corresponds to an alpha-C-aryl mannopyranose derivative. This remarkable, strained C-glycosyl compound was rapidly epimerized to the more stable 1,2-cis product on treatment with BF3.Et2O. The IDCP-reaction product could be elaborated into a 2-(alpha-C-mannopyranosyl)-3,4,5-trimethoxybenzyl alcohol derivative. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.006

文献信息

• Iodonium ion generated in situ from N-iodosuccinimide and trifluoromethanesulphonic acid promotes direct linkage of ‘disarmed’ pent-4-enyl glycosides
  作者：Peter Konradsson、David R. Mootoo、Robert E. McDevitt、Bert Fraser-Reid

  DOI：10.1039/c39900000270

  日期：——

  N-Iodosuccinimide and trifluoromethanesulphonic acid provide a powerful source of Iodonium ion which allows ‘disarmed’ pent-4-enyl glycosides that normally respond sluggishly to lodonium dicollidine perchlorate, to react rapidly and to exhibit stereodirection via neighbouring group participation of C-2 esters.

  N-碘代琥珀酰亚胺和三氟甲磺酸提供了强大的碘离子源，它使通常通常对慢二氯可乐定高氯酸钾反应迟钝的“脱甲”戊-4-烯基糖苷反应迅速，并通过C-2酯的相邻基团参与而表现出立体定向性。
• KONRADSSON, PETER;MOOTOO, DAVID R.;MCDEVITT, ROBERT E.;FRASER-REID, BERT, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 270-272
  作者：KONRADSSON, PETER、MOOTOO, DAVID R.、MCDEVITT, ROBERT E.、FRASER-REID, BERT

  DOI：——

  日期：——