Methyl 3-O-benzoyl-2-O-benzyl-6-deoxy-6-iodo-4-O-(methanesulfonyl)-α-D-glucopyranoside | 158548-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-O-benzoyl-2-O-benzyl-6-deoxy-6-iodo-4-O-(methanesulfonyl)-α-D-glucopyranoside
• CAS: 158548-92-6
• 化学式: C₂₂H₂₅IO₈S
• 分子量: 576.406
• InChiKey: JANYQQLTQFPOFD-JPVHLGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methyl 3-O-benzoyl-2-O-benzyl-6-deoxy-6-iodo-4-O-(methanesulfonyl)-α-D-glucopyranoside 在 sodium hydroxide 、 sodium azide 、 双氧水 、 碳酸氢钠 、 溶剂黄146 、 苯硫酚 、 三乙胺 、 三氟乙酸 、 tin(ll) chloride 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.0h， 生成
  参考文献：
  名称：

  Diastereoselective Synthesis of Actinobolin from D-Glucose by Application of a Novel [3 + 3] Annulation

  摘要：

  The synthesis of 5,6-O-(2-propylidene)-N-desalanyl-N-[(4-methylphenyl)methanesulfonyl]actiobolin (37) is reported. The carbocyclic ring of 37 is constructed by a novel [3 + 3] annulation method involving sequential two-electron and one-electron allylation with the conjunctive reagent 5. The 4-amino-4,6-dideoxy-D-galactose derivative 25 is efficiently prepared from D-glucose and coupled with 5. The key step in the annulation is the diastereoselective 6-endo-trig radical cyclization of the unusual thiocarbamate 32. The stereoselectivity is postulated to result from the acetonide protecting group in 32. The conversion of 37 into actinobolin has been previously established.

  DOI：

  10.1021/jo00094a040
• 作为产物：
  描述：

  Methyl 3-O-benzoyl-2-O-benzyl-4,6-bis-O-(methanesulfonyl)-α-D-glucopyranoside 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 2.0h， 以94%的产率得到Methyl 3-O-benzoyl-2-O-benzyl-6-deoxy-6-iodo-4-O-(methanesulfonyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Diastereoselective Synthesis of Actinobolin from D-Glucose by Application of a Novel [3 + 3] Annulation

  摘要：

  The synthesis of 5,6-O-(2-propylidene)-N-desalanyl-N-[(4-methylphenyl)methanesulfonyl]actiobolin (37) is reported. The carbocyclic ring of 37 is constructed by a novel [3 + 3] annulation method involving sequential two-electron and one-electron allylation with the conjunctive reagent 5. The 4-amino-4,6-dideoxy-D-galactose derivative 25 is efficiently prepared from D-glucose and coupled with 5. The key step in the annulation is the diastereoselective 6-endo-trig radical cyclization of the unusual thiocarbamate 32. The stereoselectivity is postulated to result from the acetonide protecting group in 32. The conversion of 37 into actinobolin has been previously established.

  DOI：

  10.1021/jo00094a040