methyl 6'-deoxy-β-lactoside | 129905-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6'-deoxy-β-lactoside
• CAS: 129905-24-4
• 化学式: C₁₃H₂₄O₁₀
• 分子量: 340.328
• InChiKey: GPOGAMQZTGLFEJ-ABBMIVAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.72
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 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

• 作为反应物：
  描述：

  乙酸酐 、 methyl 6'-deoxy-β-lactoside 在 吡啶 作用下， 以92%的产率得到methyl 2,2',3,3',4',6-hexa-O-acetyl-6'-deoxy-β-lactoside
  参考文献：
  名称：

  Application of protease-catalyzed regioselective esterification in synthesis of 6'-deoxy-6'-fluoro- and 6-deoxy-6-fluorolactosides

  摘要：

  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.

  DOI：

  10.1021/jo00038a036
• 作为产物：
  描述：

  methyl 6'-deoxy-6'-fluoro-2,2',3,3',4',6-hexa-O-mesitoyl-β-lactoside 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以70%的产率得到methyl 6'-deoxy-β-lactoside
  参考文献：
  名称：

  Application of protease-catalyzed regioselective esterification in synthesis of 6'-deoxy-6'-fluoro- and 6-deoxy-6-fluorolactosides

  摘要：

  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.

  DOI：

  10.1021/jo00038a036

文献信息

• Derivatives of methyl β-lactoside as substrates for and inhibitors of β-d-galactosidase from E. coli
  作者：Klaus Bock、Kim Adelhorst

  DOI：10.1016/0008-6215(90)84076-7

  日期：1990.7

  6'-deoxy derivatives of methyl beta-lactoside have been synthesised by deoxygenation at positions 2', 4', and 6', and the 3'-deoxy derivative was obtained by a glycosylation reaction. The 2'-O-methyl, 2'-O-benzyl, 2'-amino-2'-deoxy, and 1'-deuterio derivatives have been synthesized also. Only the 6'-deoxy and 1'-deuterio derivatives were substrates for the beta-D-galactosidase from E. coli, and the

  通过在位置2'，4'和6'上进行脱氧反应合成了甲基β-乳糖苷的2'-，4'-和6'-脱氧衍生物，并通过糖基化反应获得了3'-脱氧衍生物。还已经合成了2'-O-甲基，2'-O-苄基，2'-氨基-2'-脱氧和1'-氘代衍生物。只有6'-脱氧和1'-氘衍生物是大肠杆菌的β-D-半乳糖苷酶的底物，而2'-脱氧和2'-氨基-2'-脱氧衍生物是水解的有效抑制剂。酶生成甲基β-乳糖苷。