(3aS,4S,6S,7S,7aS)-7-(2-Bromo-4,5-dimethoxy-benzyloxy)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde | 484001-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,6S,7S,7aS)-7-(2-Bromo-4,5-dimethoxy-benzyloxy)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde
• 英文别名: (3aS,4S,6S,7S,7aS)-7-[(2-bromo-4,5-dimethoxyphenyl)methoxy]-4-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde
• CAS: 484001-00-5
• 化学式: C₁₉H₂₅BrO₈
• 分子量: 461.307
• InChiKey: VRNPBGIVMOQXCL-ZBRFXRBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  亚甲基三苯基膦烷 、 (3aS,4S,6S,7S,7aS)-7-(2-Bromo-4,5-dimethoxy-benzyloxy)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde 以 四氢呋喃 为溶剂， 生成 (3aS,4S,6R,7R,7aS)-7-(2-Bromo-4,5-dimethoxy-benzyloxy)-4-methoxy-2,2-dimethyl-6-vinyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
  参考文献：
  名称：

  Synthesis of chiral trans-fused pyrano[3,2-c][2]benzoxocines from d-mannose by regioselective 8-endo-aryl radical cyclization

  摘要：

  A simple chiral synthesis of trans-pyrano[3,2-c][2]benzoxocines 8a-d in good yields (60-75%) through regioselective 8-endo-trig aryl radical cyclization of the D-mannose derived enopyranosides 7a-d with Bu3SnH is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01252-2
• 作为产物：
  描述：

  甲基2,3-O-异亚丙基-alpha-D-吡喃甘露糖苷 在 咪唑 、 sodium hydroxide 、 草酰氯 、 四丁基氟化铵 、 四丁基溴化铵 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (3aS,4S,6S,7S,7aS)-7-(2-Bromo-4,5-dimethoxy-benzyloxy)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde
  参考文献：
  名称：

  Synthesis of chiral trans-fused pyrano[3,2-c][2]benzoxocines from d-mannose by regioselective 8-endo-aryl radical cyclization

  摘要：

  A simple chiral synthesis of trans-pyrano[3,2-c][2]benzoxocines 8a-d in good yields (60-75%) through regioselective 8-endo-trig aryl radical cyclization of the D-mannose derived enopyranosides 7a-d with Bu3SnH is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01252-2

文献信息

• Synthesis of chiral trans-fused pyrano[3,2-c][2]benzoxocines from d-mannose by regioselective 8-endo-aryl radical cyclization
  作者：Aniruddha Nandi、Partha Chattopadhyay

  DOI：10.1016/s0040-4039(02)01252-2

  日期：2002.8

  A simple chiral synthesis of trans-pyrano[3,2-c][2]benzoxocines 8a-d in good yields (60-75%) through regioselective 8-endo-trig aryl radical cyclization of the D-mannose derived enopyranosides 7a-d with Bu3SnH is described. (C) 2002 Elsevier Science Ltd. All rights reserved.