(4aS,6R,8aR)-2-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-6-(hydroxymethyl)-4a-methyl-3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-ol | 240133-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (4aS,6R,8aR)-2-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-6-(hydroxymethyl)-4a-methyl-3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-ol
• CAS: 240133-68-0
• 化学式: C₁₈H₃₁BrO₅
• 分子量: 407.345
• InChiKey: ZYIHHZIELXQOOT-VWYCIDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aS,6R,8aR)-2-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-6-(hydroxymethyl)-4a-methyl-3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-ol 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到[(2R,4aS,6R,8aR)-2-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-4a-methyl-3,4,6,7,8,8a-hexahydro-2H-pyrano[3,2-b]pyran-6-yl]methanol
  参考文献：
  名称：

  Novel Synthesis of the C1−C15 Polyether Domain of the Thyrsiferol and Venustatriol Natural Products

  摘要：

  [GRAPHICS]A convergent construction of the C1-C15 domain of the thyrsiferol-related natural products has been developed, This involved the separate construction of C1-C7 and C8-C15 fragments, their organochromic-mediated coupling, and subsequent reductive closure of the a ring. This synthetic A-B-C ring construct will be useful for the total synthesis of the biologically active polyether squalenoid natural products, as well as their non-natural analogues.

  DOI：

  10.1021/ol990648k
• 作为产物：
  描述：

  (R)-γ-羟甲基-γ-丁内酯 (R)-4,5-二氢-5-羟甲基-2(3H)-呋喃酮 (R)-5-羟甲基-2-氧代四氢呋喃 在 palladium dihydroxide 咪唑 、 chromium dichloride 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 manganese(IV) oxide 、 pyridine-SO3 complex 、 D-(-)-酒石酸二乙酯 、 三氟甲磺酸 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 癸烷 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 正戊烷 、 苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 97.08h， 生成 (4aS,6R,8aR)-2-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-6-(hydroxymethyl)-4a-methyl-3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-ol
  参考文献：
  名称：

  Novel Synthesis of the C1−C15 Polyether Domain of the Thyrsiferol and Venustatriol Natural Products

  摘要：

  [GRAPHICS]A convergent construction of the C1-C15 domain of the thyrsiferol-related natural products has been developed, This involved the separate construction of C1-C7 and C8-C15 fragments, their organochromic-mediated coupling, and subsequent reductive closure of the a ring. This synthetic A-B-C ring construct will be useful for the total synthesis of the biologically active polyether squalenoid natural products, as well as their non-natural analogues.

  DOI：

  10.1021/ol990648k

文献信息

• Novel Synthesis of the C1−C15 Polyether Domain of the Thyrsiferol and Venustatriol Natural Products
  作者：Isabel C. González、Craig J. Forsyth

  DOI：10.1021/ol990648k

  日期：1999.7.1

  [GRAPHICS]A convergent construction of the C1-C15 domain of the thyrsiferol-related natural products has been developed, This involved the separate construction of C1-C7 and C8-C15 fragments, their organochromic-mediated coupling, and subsequent reductive closure of the a ring. This synthetic A-B-C ring construct will be useful for the total synthesis of the biologically active polyether squalenoid natural products, as well as their non-natural analogues.