methyl (methyl 2-O-acetyl-β-D-galactopyranosid)uronate | 147488-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 2-O-acetyl-β-D-galactopyranosid)uronate
• CAS: 147488-82-2
• 化学式: C₁₀H₁₆O₈
• 分子量: 264.232
• InChiKey: JXKLXAVQXJVTFE-WASRKXDBSA-N

物化性质

• 沸点：
  363.5±42.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.82
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl 2-O-acetyl-β-D-galactopyranosid)uronate 在 吡啶 、 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl (methyl 2,4-di-O-acetyl-3-O-trityl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of a heteroglycuronan derivative containingthe β-

  摘要：

  Helferich glycosylation of the cyanoethylidene L-rhamnose derivative 3 with the galactosyluronic bromide 2 gave the disaccharide 4 as a key intermediate in the synthesis of the monomer 13 for trityl-cyanoethylidene condensation (TCC). The following formation of the monomer 13, including introduction of a trityl group at O-3', proceeded in six steps. Because of the difficulty of some steps, an alternative route for 13 was tested. Model compounds 20, 21, and 22 were synthesized in order to confirm the stereoregularity of the products of the polycondensation. The polycondensation of the monomer gave D-GalpA-(1 --> 3)-L-Rha-oligomer derivatives consisting mainly of three repeating units. This result is in contrast with the degree of polymerisation (dp greater-than-or-equal-to 22) of other synthetic rhamnans, but is very similar to dp 2-7 of homo- and hetero-glucuronan derivatives.

  DOI：

  10.1016/s0008-6215(92)84238-n
• 作为产物：
  描述：

  methyl (methyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosid)uronate 在 三氟乙酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.33h， 以90%的产率得到methyl (methyl 2-O-acetyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of a heteroglycuronan derivative containingthe β-

  摘要：

  Helferich glycosylation of the cyanoethylidene L-rhamnose derivative 3 with the galactosyluronic bromide 2 gave the disaccharide 4 as a key intermediate in the synthesis of the monomer 13 for trityl-cyanoethylidene condensation (TCC). The following formation of the monomer 13, including introduction of a trityl group at O-3', proceeded in six steps. Because of the difficulty of some steps, an alternative route for 13 was tested. Model compounds 20, 21, and 22 were synthesized in order to confirm the stereoregularity of the products of the polycondensation. The polycondensation of the monomer gave D-GalpA-(1 --> 3)-L-Rha-oligomer derivatives consisting mainly of three repeating units. This result is in contrast with the degree of polymerisation (dp greater-than-or-equal-to 22) of other synthetic rhamnans, but is very similar to dp 2-7 of homo- and hetero-glucuronan derivatives.

  DOI：

  10.1016/s0008-6215(92)84238-n