tert-Butyl 3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-talo-pyranoside | 131267-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl 3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-talo-pyranoside
• CAS: 131267-48-6
• 化学式: C₁₄H₂₃IO₆
• 分子量: 414.238
• InChiKey: ZQRAUGRLKASSAY-HONSUDCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 、 叔丁醇 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以8.8%的产率得到tert-Butyl 3,4-di-O-acetyl-2,6-dideoxy-2-iodo-β-L-galacto-pyranoside
  参考文献：
  名称：

  Iodoalkoxylation of 1,5-anhydro-2-deoxy-hex-1-enitols (glycals)

  摘要：

  Exclusive trans-addition is observed in the iodoalkoxylation of the 6-membered cyclic enol ethers 3,4-di-O-acetyl-L-rhamnal (1), 3,4-di-O-acetyl-L-fucal (2), and related glycal derivatives. The main products from 1 and from 3,4,6-tri-O-acetyl-D-glucal (3) thus had the alpha-manno configuration. Similarly, alpha-talo products were obtained from 2 in 87-93% yield. The product distribution is not affected by the electronegativity of the 5-substituent. It is concluded that steric factors in the glycal and the nucleophile affect only the step of trans-diaxial opening of the intermediate iodonium ion. Enhanced yields of the desired trans-diaxial products were observed in reactions of glycals having the lyxo configuration when the reactions were conducted in tetrahydrofuran or methanol.

  DOI：

  10.1016/0008-6215(90)80129-q