methyl 6-deoxy-6-fluoro-β-lactoside | 141485-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-fluoro-β-lactoside
• CAS: 141485-13-4
• 化学式: C₁₃H₂₃FO₁₀
• 分子量: 358.318
• InChiKey: KKMZUFZHQPKVQQ-ABBMIVAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.77
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158.3
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 二乙胺基三氟化硫 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.05h， 生成 methyl 6-deoxy-6-fluoro-β-lactoside
  参考文献：
  名称：

  合成所有可能的单甲基醚和甲基β-乳糖苷的几种脱氧卤代类似物，作为蓖麻蓖麻凝集素的配体。

  摘要：

  甲基β-内酯（1）的所有可能的单甲基醚的合成已从1直接进行，利用了烷基化和甲锡烷基化反应中羟基的不同反应性。另外，通过适当的底物与二乙基氨基三氟化硫或氟化四丁基铵的反应制备了在6,3'，4'，epi-4'和6'位置的1的脱氧氟衍生物。最后，还制备了1的6-脱氧碘和6'-溴脱氧氧基类似物。

  DOI：

  10.1016/0008-6215(94)84243-4

文献信息

• Application of protease-catalyzed regioselective esterification in synthesis of 6'-deoxy-6'-fluoro- and 6-deoxy-6-fluorolactosides
  作者：Shaopei Cai、Senitiroh Hakomori、Tatsushi Toyokuni

  DOI：10.1021/jo00038a036

  日期：1992.6

  Subtilisin-catalyzed esterification of methyl 4-O-beta-D-galactopyranosyl-beta-D-glucopyranoside (methyl beta-lactoside) (1) with 2,2,2-trichloroethyl butyrate (3) distinguished between the two primary hydroxyl groups of 1, yielding exclusively the 6'-O-monobutyryl derivative 6 from which 6'-deoxy-6'-fluoro- and 6-deoxy-6-fluorolactosides (22 and 29, respectively) were efficiently synthesized. A key feature in the synthesis of 22 was the use of the 2,4,6-trimethylbenzoyl (mesitoyl) group to protect the remaining free hydroxyl groups. A mesitoate ester, in addition to being inert to the condition that hydrolyzed a butyrate ester, could be easily cleaved by reduction with AlH3 without hydrogenolysis of a C-F bond. The steric bulk of a mesitoyl group suppressed the C-4' --> C-6' acyl migration during the fluorination with (diethylamino)sulfur trifluoride (DAST). The success in the synthesis of 29 depended on the choice of solvent employed for the DAST fluorination. With diglyme the desired 6-fluoro derivative 28 was the only product, whereas the use of CH2Cl2 yielded 6-O-methyl-beta-lactosyl fluoride 30 concomitantly through a C-1 --> C-6 migration of the methoxyl group.