(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(3,5-dimethoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran | 647832-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(3,5-dimethoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran
• CAS: 647832-35-7
• 化学式: C₄₁H₄₈O₈
• 分子量: 668.827
• InChiKey: BGXBYZRPJZMKPE-HJRBIJKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  49.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(3,5-dimethoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran 在 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 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：

  (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 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(3,5-dimethoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-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