3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-glucopyranosyl chloride | 103321-18-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-glucopyranosyl chloride
• 英文别名: [(2S,3S,4R,5S,6S)-4-acetyloxy-5,6-dichloro-2-methyloxan-3-yl] acetate
• CAS: 103321-18-2
• 化学式: C₁₀H₁₄Cl₂O₅
• 分子量: 285.124
• InChiKey: FBIFULIAMTVFMQ-NSGULZDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 氯 作用下， 以 四氯化碳 为溶剂， 反应 0.17h， 以10%的产率得到3,4-di-O-acetyl-2-chloro-2,6-dideoxy-β-L-mannopyranosyl chloride
  参考文献：
  名称：

  Halogenation of 1,5-anhydrohex-1-enitols (glycals). Influence of the C-6 substituent

  摘要：

  DOI：

  10.1021/jo00368a015

文献信息

• Synthesis and antitumor activity of 2′-bromo- and 2′-chloro-3′-acetoxy-3′-deaminodaunorubicin analogs
  作者：Derek Horton、Waldemar Priebe、Oscar Varela

  DOI：10.1016/s0008-6215(00)90678-5

  日期：1985.12

  Bromination of 3,4-di-O-acetyl-L-rhamnal (7) and subsequent glycosidic coupling under Koenigs-Knorr conditions with daunomycinone gave a mixture of three compounds having the beta-L-gluco (10), alpha-L-gluco (11), and alpha-L-manno (12) configurations. Analogous bromination of 3,4-di-O-acetyl-L-fucal (13) followed by coupling with daunomycinone gave a mixture of three glycosides having the beta-L-galacto (16), alpha-L-galacto (17), and alpha-L-talo (18) configurations. Chlorination of 7 and coupling with daunomycinone in the presence of silver triflate gave products having the alpha-L-gluco (21) and alpha-L-manno (22) configurations, whereas 13, under similar conditions, gave only one stereoisomeric product, that having the alpha-L-galacto (24) configuration. Compounds 12 and 22 showed high in vivo activity in the P-388 lymphocytic leukemia assay.