(3aR,5R,6S,6aR)-6-(2-bromo-4,5-dimethyloxy-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole | 417702-87-5

• 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-4,5-dimethyloxy-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-4,5-dimethoxy-benzyloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole；3-O-(2-bromo-4,5-dimethoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside；(3aR,5R,6S,6aR)-6-[(2-bromo-4,5-dimethoxyphenyl)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: 417702-87-5
• 化学式: C₂₁H₂₉BrO₈
• 分子量: 489.36
• InChiKey: MEWMJNHVKIDFTO-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-6-(2-bromo-4,5-dimethyloxy-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-{(S)-[(3aR,5R,6S,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid methyl ester
  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：

  2-溴-4,5-二甲氧基溴苄 、 双丙酮葡萄糖 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 以75%的产率得到(3aR,5R,6S,6aR)-6-(2-bromo-4,5-dimethyloxy-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：

  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

文献信息

• 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：——
• Sequential Baylis–Hillman reaction and radical cyclization of furanose derivatives: expeditious approach to enantiopure benzo-fused nine-membered oxacycles
  作者：Tirtha Pada Majhi、Arpita Neogi、Soumen Ghosh、Alok Kumar Mukherjee、Partha Chattopadhyay

  DOI：10.1016/j.tet.2006.09.080

  日期：2006.12

  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.