(3aR,4S,5aR,8R,9aR,9bS)-2,2-Dibutyl-4-methoxy-8-phenyl-hexahydro-1,3,5,7,9-pentaoxa-2-stanna-cyclopenta[a]naphthalene | 77449-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (3aR,4S,5aR,8R,9aR,9bS)-2,2-Dibutyl-4-methoxy-8-phenyl-hexahydro-1,3,5,7,9-pentaoxa-2-stanna-cyclopenta[a]naphthalene
• 英文别名: (1R,2S,6R,7S,9R,12R)-4,4-dibutyl-7-methoxy-12-phenyl-3,5,8,11,13-pentaoxa-4-stannatricyclo[7.4.0.02,6]tridecane
• CAS: 77449-14-0
• 化学式: C₂₂H₃₄O₆Sn
• 分子量: 513.218
• InChiKey: VSLBEHSIBDGHIP-YIMMVXISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4S,5aR,8R,9aR,9bS)-2,2-Dibutyl-4-methoxy-8-phenyl-hexahydro-1,3,5,7,9-pentaoxa-2-stanna-cyclopenta[a]naphthalene 在 盐酸 、 potassium fluoride 、 3 A molecular sieve 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 31.0h， 生成 Methyl 3-O-allyl-2,4-di-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Adenophostin Analogues Lacking the Adenine Moiety as Novel Potent IP₃ Receptor Ligands:  Some Structural Requirements for the Significant Activity of Adenophostin A

  摘要：

  1-O-Tetrahydrofuranyl-alpha-D-glucopyranose derivatives 5-8 were designed and synthesized as novel IP3 receptor ligands. The glycosidation reactions between fluoroglycosyl donor 23 and tetrahydrofuran derivatives 11-14 as glycosyl accepters selectively gave the corresponding alpha-glycosides, which were converted into the target Compounds 5-8 via the introduction of phosphate groups using the phosphoramidite method. Among these compounds, 1-O-tetrahydrofuranyl-alpha-D-glucopyranose trisphosphate derivatives 5 and 8 significantly inhibited the binding of [H-3] IP3 to IP3 receptor from porcine cerebella, with IC50 values of 25 and 27 nM, respectively, which were comparable to the affinity of IP3 itself.

  DOI：

  10.1021/jo980925l
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 camphor-10-sulfonic acid 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 94.5h， 生成 (3aR,4S,5aR,8R,9aR,9bS)-2,2-Dibutyl-4-methoxy-8-phenyl-hexahydro-1,3,5,7,9-pentaoxa-2-stanna-cyclopenta[a]naphthalene
  参考文献：
  名称：

  D-葡萄糖立体控制合成乌头碱 D 环

  摘要：

  描述了从 ( D )-(+)-葡萄糖合成完全氧化的乌头碱 D 环前体。该路线的特点是高度非对映选择性的炔基格氏酮加成和碱基介导的烯内酯至 1,3-二酮重排。

  DOI：

  10.1039/d4ob00561a

文献信息

• Grindley, T. Bruce; Thangarasa, Rasiah, Canadian Journal of Chemistry, 1990, vol. 68, # 7, p. 1007 - 1019
  作者：Grindley, T. Bruce、Thangarasa, Rasiah

  DOI：——

  日期：——
• Namazi, H.; Sharifzadeh, R., Molecules, 2005, vol. 10, # 3, p. 749 - 759
  作者：Namazi, H.、Sharifzadeh, R.

  DOI：——

  日期：——
• On the selectivity of stannylene-mediated alkylation and esterification of methyl 4,6-O-benzylidene α-d-glucopyranoside
  作者：David J. Jenkins、Barry V.L. Potter

  DOI：10.1016/0008-6215(94)00221-5

  日期：1994.12