Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester | 622832-75-1

• 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: Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester
• CAS: 622832-75-1
• 化学式: C₂₉H₃₀O₅
• 分子量: 458.554
• InChiKey: ZRZWUOAFXSKMGW-VJLHXPKFSA-N

物化性质

• 沸点：
  578.6±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 ((1R,2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-7-oxabicyclo-[4.1.0]heptan-2-yl)methanol (+)-2,3,4-tri-O-benzylcyclophellitol
  参考文献：
  名称：

  Conversion of d-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction:  Application to Total Synthesis of (+)-Cyclophellitol

  摘要：

  [GRAPHICS]A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4,5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-Cl and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.

  DOI：

  10.1021/ol035424n
• 作为产物：
  描述：

  (1R,2R,3S,4S,5S)-2,3,4-tris(benzyloxy)-5-hydroxy-7-aza-8-oxabicyclo[4.3.0]non-6-ene 在 hexacarbonyl molybdenum 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 115.0h， 生成 Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester
  参考文献：
  名称：

  Conversion of d-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction:  Application to Total Synthesis of (+)-Cyclophellitol

  摘要：

  [GRAPHICS]A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4,5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-Cl and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.

  DOI：

  10.1021/ol035424n