(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole | 200346-52-7

• 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-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole；(3aR,5R,6S,6aR)-6-(2-bromobenzyloxy)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxole；6-(2-bromobenzyloxy)-5-(2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole；3-O-(2-bromobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside；(3aR,5R,6S,6aR)-6-[(2-bromophenyl)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: 200346-52-7
• 化学式: C₁₉H₂₅BrO₆
• 分子量: 429.308
• InChiKey: DPEGICJVBFKPDY-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 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,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 在 三乙烯二胺 、 sodium periodate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 27.0h， 生成 2-{[(3aR,5R,6S,6aR)-6-(2-Bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylonitrile
  参考文献：
  名称：

  Sequential Baylis–Hillman reaction and radical cyclization of furanose derivatives: expeditious approach to enantiopure benzo-fused nine-membered oxacycles

  摘要：

  A regioselective 9-endo-trig aryl radical cyclization of D-glucose derived diastereomeric Baylis-Hillman reaction products with Bu3SnH led to highly functionalized tricyclic benzannulated ethers incorporating cis- and trans-9,5 bicyclic systems in good yields. Degradation of one of the products afforded an enantiopure multifunctionalized benzoxonine derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.080
• 作为产物：
  描述：

  双丙酮葡萄糖 、 2-溴溴苄 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  钯催化的分子内 C-O 键形成：一种合成手性苯并二恶辛的方法

  摘要：

  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)

  DOI：

  10.1002/ejoc.200700762

文献信息

• 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)
• 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。
• 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.
• 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：——
• US4429119A
  申请人：——

  公开号：US4429119A

  公开（公告）日：1984-01-31