Acetic acid (2R,3R,4R,6S)-4-chloro-6-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester | 69718-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,6S)-4-chloro-6-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,4R,6S)-4-chloro-6-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 69718-69-0
• 化学式: C₈H₁₃ClO₄
• 分子量: 208.642
• InChiKey: QFWNKVZNGYGHMC-CCXZUQQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,6R)-4,6-dichloro-2-methyl-tetrahydro-pyran-3-yl ester 在 水 、 silver carbonate 作用下， 以 丙酮 为溶剂， 生成 Acetic acid (2R,3R,4R,6S)-4-chloro-6-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of sugar-ring hydroxyl analogs of daunorubicin

  摘要：

  Daunorubicin analogues in which the natural amino sugar, daunosamine, is replaced by neutral 2,6-dideoxy-hexopyranosyl residues have been prepared in high yields. Glycosidation of 3,4-di-O-acetyl-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl chloride (13) with daunomycinone under Koenigs-Knorr conditions yielded exclusively the protected alpha-anomeric product 4, which was converted into the free glycoside 5. In contrast, the 1-chloro-D-ribo isomer 19, bearing p-nitrobenzoyl groups for hydroxyl-group protection, furnished a 5:3 mixture of the alpha (6) and beta (7) glycosides. Separation and individual deprotection afforded the target compounds 8 (from 6) and 9 (from 7). Whereas all of the D-ribo analogues (6--9) are inactive as antitumor agents in vivo against P388 lymphocytic leukemia in mice, the protected L-lyxo glycoside 4 (T/C 186) and also the free glycoside 5 (T/C 183) are highly effective in this test system; 5 is also active (T/C 146) in vivo against murine B16 melanocarcinoma.

  DOI：

  10.1021/jm00190a010