(S)-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-phenylmethanol | 1385036-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-phenylmethanol
• CAS: 1385036-04-3
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: JZYGRNZJVVAWPN-RYMFRWLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 、 苯硼酸 在 diethylzinc 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以78%的产率得到(S)-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-phenylmethanol
  参考文献：
  名称：

  Diastereoselective Addition of Arylzinc Reagents to Sugar Aldehydes

  摘要：

  The diastereoselective arylation of sugar-derived aldehydes is described. The arylating reagents are generated in situ by a boron-to-zinc exchange reaction of arylboronic acids with Et2Zn to generate arylethylzinc reagents. The exquisite reactivity of the arylzinc reagents allowed for an efficient and mild arylation, delivering the corresponding products in diastereolsomeric ratios of up to >20:1. The utility of the methodology is highlighted with an efficient formal synthesis of (+)-7-epl-goniofufurone, a member of the styryllactone family of natural products.

  DOI：

  10.1021/ol301724x

文献信息

• Diastereoselective Addition of Arylzinc Reagents to Sugar Aldehydes
  作者：Ana D. Wouters、Diogo S. Lüdtke

  DOI：10.1021/ol301724x

  日期：2012.8.3

  The diastereoselective arylation of sugar-derived aldehydes is described. The arylating reagents are generated in situ by a boron-to-zinc exchange reaction of arylboronic acids with Et2Zn to generate arylethylzinc reagents. The exquisite reactivity of the arylzinc reagents allowed for an efficient and mild arylation, delivering the corresponding products in diastereolsomeric ratios of up to >20:1. The utility of the methodology is highlighted with an efficient formal synthesis of (+)-7-epl-goniofufurone, a member of the styryllactone family of natural products.