allyl 2-O-(4-methoxybenzyl)-3,4,6-O-tri-acetyl-β-D-galactopyranoside | 914097-74-8

• 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: allyl 2-O-(4-methoxybenzyl)-3,4,6-O-tri-acetyl-β-D-galactopyranoside
• 英文别名: allyl 2-O- (4-methoxylbenzyl)-3,4,6-O-triacetyl-β-D-galactopyranoside；Mob(-2)Gal3Ac4Ac6Ac(b)-O-allyl；[(2R,3S,4S,5R,6R)-3,4-diacetyloxy-5-[(4-methoxyphenyl)methoxy]-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 914097-74-8
• 化学式: C₂₃H₃₀O₁₀
• 分子量: 466.485
• InChiKey: AWJPAFPNFIOQBH-BMXMUORJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  allyl 2-O-(4-methoxybenzyl)-3,4,6-O-tri-acetyl-β-D-galactopyranoside 在 三乙基硅烷 、 四(三苯基膦)钯 、 molecular sieve 、 三氟甲磺酸三甲基硅酯 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 allyl 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells

  摘要：

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.

  DOI：

  10.1021/ol062199b
• 作为产物：
  描述：

  allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 allyl 2-O-(4-methoxybenzyl)-3,4,6-O-tri-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells

  摘要：

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.

  DOI：

  10.1021/ol062199b

文献信息

• Red Algal Molecules - Synthesis of Methyl Neo-β-carrabioside and Its <i>S</i>-Linked Variant via Two Synthetic Routes: A Late Stage Ring Closure and Using a 3,6-Anhydro-<scp>d</scp>-galactosyl Donor
  作者：Michael D. Wallace、Elizabeth Ficko-Blean、Keith A. Stubbs

  DOI：10.1021/acs.joc.0c02339

  日期：2020.12.18

  the identification and characterization of marine bacterial exo-α-3,6-anhydro-d-galactosidases that have specific activity on red algal neo-carrageenan oligosaccharides, such as those found in both family 127 and 129 of the glycoside hydrolases. In addition a biochemical assay using the synthesized methyl neo-β-carrabioside and the marine bacterial exo-α-3,6-anhydro-d-galactosidase ZgGH129 demonstrates

  首次合成了新的β-角菜糖甲基，采用后期闭环方法安装所需的3,6-脱水桥或合适的3,6-脱水半乳糖基供体以形成不利的1,2 -顺-赤道α-键。使用晚期闭环方法，还实现了甲基新β-角菜糖苷的S-连接类似物。这些化合物可用于鉴定和表征海洋细菌exo -α-3,6-脱水-d-半乳糖苷酶对红色藻类新角叉菜聚糖寡糖具有特定活性，例如在糖苷水解酶的127和129家族中发现的那些。此外生化测定使用合成的甲基新β-carrabioside和海洋细菌外-α-3,6-脱水- d半乳糖苷酶ZG GH129证明，对于所述酶的最小基板单元是新β-carrabiose。