(5R,6R,7S,8R)-6,7,8-tris(phenylmethoxy)-5-(phenylmethoxymethyl)-1,4-dioxaspiro[2.5]octane | 131603-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,6R,7S,8R)-6,7,8-tris(phenylmethoxy)-5-(phenylmethoxymethyl)-1,4-dioxaspiro[2.5]octane
• CAS: 131603-38-8；136773-95-0
• 化学式: C₃₅H₃₆O₆
• 分子量: 552.667
• InChiKey: SHSFNFBWCZFTPY-BMURFIBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diacetone-D-glucose 、 (5R,6R,7S,8R)-6,7,8-tris(phenylmethoxy)-5-(phenylmethoxymethyl)-1,4-dioxaspiro[2.5]octane 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-[(3aR,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-2-yl}-methanol
  参考文献：
  名称：

  Epoxidation of exoxyclic glycals: A new access to glycosides of ketosugars

  摘要：

  A novel approach to the synthesis of glycosides and disaccharides of ketofuranoses and ketopyranoses by epoxidation of exocyclic glycals and reaction of the intermediate epoxides with different alcohols is described.

  DOI：

  10.1016/0040-4039(91)80621-c
• 作为产物：
  描述：

  2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (5R,6R,7S,8R)-6,7,8-tris(phenylmethoxy)-5-(phenylmethoxymethyl)-1,4-dioxaspiro[2.5]octane
  参考文献：
  名称：

  Epoxidation of exoxyclic glycals: A new access to glycosides of ketosugars

  摘要：

  A novel approach to the synthesis of glycosides and disaccharides of ketofuranoses and ketopyranoses by epoxidation of exocyclic glycals and reaction of the intermediate epoxides with different alcohols is described.

  DOI：

  10.1016/0040-4039(91)80621-c

文献信息

• Epoxidation of exoxyclic glycals: A new access to glycosides of ketosugars
  作者：Francesco Nicotra、Luigi Panza、Giovanni Russo

  DOI：10.1016/0040-4039(91)80621-c

  日期：1991.8

  A novel approach to the synthesis of glycosides and disaccharides of ketofuranoses and ketopyranoses by epoxidation of exocyclic glycals and reaction of the intermediate epoxides with different alcohols is described.
• Studies on the synthesis of C-Glycoside sulfones as potential glycosyl transferase inhibitors
  作者：Jacquelyn Gervay、Terrence M. Flaherty、Daniel Holmes

  DOI：10.1016/s0040-4020(97)01021-1

  日期：1997.12

  beta-C-Glycoside sulfoxides and sulfones were prepared by radical addition of thiol acetic acid to exocyclic glycals followed by deacetylation, S-alkylation, and selective oxidation. These compounds are representative examples of a new class of molecules designed to be glycosyl transferase inhibitors. (C) 1997 Elsevier Science Ltd.