(3aR,5R,6S,6aR)-6-(2-bromo-5-methoxy-benzyloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole | 200346-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,5R,6S,6aR)-6-(2-bromo-5-methoxy-benzyloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6S,6aR)-6-(2-bromo-5-methoxybenzyloxy)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxole；3-O-(2-bromo-5-methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside；(3aR,5R,6S,6aR)-6-[(2-bromo-5-methoxyphenyl)methoxy]-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 200346-53-8
• 化学式: C₂₀H₂₇BrO₇
• 分子量: 459.334
• InChiKey: HLVHXINAKALTGA-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-6-(2-bromo-5-methoxy-benzyloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 偶氮二异丁腈 、 potassium tert-butylate 、 碘 、 三正丁基氢锡 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 苯 为溶剂， 反应 35.5h， 生成 (3aR,3bS,10aR,11aR)-7-methoxy-2,2-dimethyl-3a,3b,5,10,10a,11a-hexahydro-1,3,4,11-tetraoxa-benzo[f]cyclopenta[a]azulene
  参考文献：
  名称：

  Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives

  摘要：

  Tributyltin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives 5a-c led to the highly functionalized cis-fused bicyclic ethers 6a-c. The product could subsequently be transformed to the optically active tricyclic nucleoside analogue 8 or oxepine derivative 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.054
• 作为产物：
  描述：

  2-溴-5-甲氧基溴苄 、 双丙酮葡萄糖 在 四丁基溴化铵 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70.5%的产率得到(3aR,5R,6S,6aR)-6-(2-bromo-5-methoxy-benzyloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
  参考文献：
  名称：

  A simple construction of chiral fused benzoxocine ring ethers from D-glucose by regioselective 8-endo-aryl radical cyclisation

  摘要：

  5,6-脱氧-D-木基-5-烯呋喃苷 3a 和 3b 与三正丁基氢化锡进行区域选择性 8-内三芳基自由基环化，得到手性呋喃[3,2-c][2]苯并氧辛4a和4b的良率良好；报道了4a的晶体结构。

  DOI：

  10.1039/a706249d

文献信息

• A simple construction of chiral fused benzoxocine ring ethers from D-glucose by regioselective 8-endo-aryl radical cyclisation
  作者：Partha Chattopadhyay、Monika Mukherjee、Soma Ghosh

  DOI：10.1039/a706249d

  日期：——

  A regioselective 8-endo-trig aryl radical cyclisation of the 5,6-deoxy-D-xylo-5-enofuranosides 3a and 3b with tri-n-butyltin hydride provides the chiral furo[3,2-c][2]benzoxocines 4a and 4b in good yields; the crystal structure of 4a is reported.

  5,6-脱氧-D-木基-5-烯呋喃苷 3a 和 3b 与三正丁基氢化锡进行区域选择性 8-内三芳基自由基环化，得到手性呋喃[3,2-c][2]苯并氧辛4a和4b的良率良好；报道了4a的晶体结构。
• Nandi; Mukhopadhyay; Chattopadhyay, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 24, p. 3346 - 3351
  作者：Nandi、Mukhopadhyay、Chattopadhyay

  DOI：——

  日期：——
• Palladium-Catalyzed Intramolecular C–O Bond Formation: An Approach to the Synthesis of Chiral Benzodioxocines
  作者：Arpita Neogi、Tirtha P. Majhi、Basudeb Achari、Partha Chattopadhyay

  DOI：10.1002/ejoc.200700762

  日期：2008.1

  Palladium-catalyzed intramolecular aryl etherification using bulky binaphthylphosphane or bis(diphenylphosphanyl)ferrocene ligands is shown to be a convenient method for the synthesis of eight-membered oxygen heterocycles. Application of this methodology to a sugar derivative led to the synthesis of chiral benzodioxocine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  钯催化的分子内芳基醚化使用笨重的联萘膦或双（二苯基膦基）二茂铁配体被证明是一种合成八元氧杂环的方便方法。将此方法应用于糖衍生物导致合成手性苯并二恶辛。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives
  作者：Arpita Neogi、Tirtha Pada Majhi、Nanda Ghoshal、Partha Chattopadhyay

  DOI：10.1016/j.tet.2005.07.054

  日期：2005.9

  Tributyltin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives 5a-c led to the highly functionalized cis-fused bicyclic ethers 6a-c. The product could subsequently be transformed to the optically active tricyclic nucleoside analogue 8 or oxepine derivative 9. (c) 2005 Elsevier Ltd. All rights reserved.