Benzoic acid (2R,3R,4S,5S,6R)-2-acetoxy-3-benzyloxy-5-ethoxycarbonylamino-6-methyl-tetrahydro-pyran-4-yl ester | 158549-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3R,4S,5S,6R)-2-acetoxy-3-benzyloxy-5-ethoxycarbonylamino-6-methyl-tetrahydro-pyran-4-yl ester
• CAS: 158549-01-0
• 化学式: C₂₅H₂₉NO₈
• 分子量: 471.507
• InChiKey: YOZQSFPLBDFMBT-IZIQSIKJSA-N

物化性质

• 沸点：
  592.6±50.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3R,4S,5S,6R)-2-acetoxy-3-benzyloxy-5-ethoxycarbonylamino-6-methyl-tetrahydro-pyran-4-yl ester 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 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 4-azido-3-O-benzoyl-2-O-benzyl-4,6-dideoxy-α-D-galactopyranoside 在 碳酸氢钠 、 苯硫酚 、 三乙胺 、 三氟乙酸 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 21.0h， 生成 Benzoic acid (2R,3R,4S,5S,6R)-2-acetoxy-3-benzyloxy-5-ethoxycarbonylamino-6-methyl-tetrahydro-pyran-4-yl ester
  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