2,3,4-tri-O-acetyl-6-deoxy-α-D-galactopyranose | 157365-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-6-deoxy-α-D-galactopyranose
• 英文别名: (2S,3R,4S,5S,6R)-2-Hydroxy-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate；[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 157365-62-3
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: QHOCNNVTMIFDFP-UOORRKKPSA-N

物化性质

• 沸点：
  358.7±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-deoxy-α-D-galactopyranose 在 2,4,6-三甲基吡啶 、 lead(IV) acetate 、 sodium hydroxide 、 Dowex 1X₈ (HCO₃^-) 、 水 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 160.0h， 生成 evomonoside
  参考文献：
  名称：

  Synthesis of Uridine 5′-(α-D-Fucopyranosyl Diphosphate) and (Digitoxigenin-3β-yl)-β-D-Fucopyranoside and Enzymatic β-D-Fucosylation of Cardenolide Aglycones in Digitalis lanata1

  摘要：

  The phosphorylation of 2,3,4-tri-O-acetyl-alpha-D-fucopyranose with o-phenylene phosphochloridate yielded alpha-D-fucopyranosyl phosphate which was used for condensation with uridine 5'-monophosphomorpholidate to give uridine 5'-(alpha-D-fucopyranosyl diphosphate) (UDP-alpha-D-fucose). A crude enzyme preparation from young leaves of Digitalis lanata EHRH has been shown to catalyze the transfer of D-fucose from synthetic UDP-alpha-D-fucose to cardenolide aglycones, such as digitoxigenin. The reaction product was identified and characterized by chemical synthesis, HPLC, and spectral methods as the 3 beta-O-beta-D-fucopyranoside of digitoxigenin (digiproside). (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1012
• 作为产物：
  描述：

  D-Fucose 在 吡啶 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 2,3,4-tri-O-acetyl-6-deoxy-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of Uridine 5′-(α-D-Fucopyranosyl Diphosphate) and (Digitoxigenin-3β-yl)-β-D-Fucopyranoside and Enzymatic β-D-Fucosylation of Cardenolide Aglycones in Digitalis lanata1

  摘要：

  The phosphorylation of 2,3,4-tri-O-acetyl-alpha-D-fucopyranose with o-phenylene phosphochloridate yielded alpha-D-fucopyranosyl phosphate which was used for condensation with uridine 5'-monophosphomorpholidate to give uridine 5'-(alpha-D-fucopyranosyl diphosphate) (UDP-alpha-D-fucose). A crude enzyme preparation from young leaves of Digitalis lanata EHRH has been shown to catalyze the transfer of D-fucose from synthetic UDP-alpha-D-fucose to cardenolide aglycones, such as digitoxigenin. The reaction product was identified and characterized by chemical synthesis, HPLC, and spectral methods as the 3 beta-O-beta-D-fucopyranoside of digitoxigenin (digiproside). (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1012

文献信息

• Harnessing the Dual Properties of Thiol-Grafted Cellulose Paper for Click Reactions: A Powerful Reducing Agent and Adsorbent for Cu
  作者：Jordi Rull-Barrull、Martin d'Halluin、Erwan Le Grognec、François-Xavier Felpin

  DOI：10.1002/anie.201606760

  日期：2016.10.17

  new approach exploiting the dual properties of thiol‐grafted cellulose paper for promoting copper‐catalyzed [3+2]‐cycloadditions of organic azides with alkynes and adsorbing residual copper species in solution was developed. The thiol‐grafted cellulose paper, used as a paper strip, effects the reduction of CuII to catalytically active CuI and acts as a powerful adsorbent for copper, thereby facilitating

  开发了一种新方法，该方法利用硫醇接枝纤维素纸的双重特性来促进炔烃与有机叠氮化物的铜催化[3 + 2]-环加成反应，并吸附溶液中的残留铜物种。用作纸带的硫醇接枝纤维素纸可将Cu II还原为催化活性Cu I，并作为强力的铜吸附剂，从而简化了后处理过程，并使粗混合物几乎不含铜残留物一次过滤后。
• Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2‐Aryl‐1,3‐dithiane 1‐Oxide ^†
  作者：Lei Cai、Jing Zeng、Ting Li、Ying Xiao、Xiang Ma、Xiong Xiao、Qin Zhang、Lingkui Meng、Qian Wan

  DOI：10.1002/cjoc.201900419

  日期：2020.1

  center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3‐diol protection. Most

  利用三氟甲磺酸酐（Tf 2O）。通过将高亲硫性启动子系统的高效性与脱水糖基化的逐步效率相结合，该试剂通过C1-半乙缩醛供体进行了分子间的氧代硫代缩醛化反应，以安装一个临时的离去基团，从而使远程位置的瞬变亲电子中心变为异头位置。拴在末端的三氟甲磺酸亚砜在分子内同时活化了硫化物，提供了碳碳鎓离子，从而促进了标题糖基化。除了可容纳广泛的官能团和不活跃的半缩醛底物外，目前的激活方案还证明了对1,3-二醇的保护是合宜的。最重要的是，该方法进一步为将硫化学应用于碳水化合物化学提供了新的视角。
• Enzymic transfer of 6-modified d-galactosyl residues: synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-d-galactose residues at the nonreducing end and evaluation of 6-deoxy-d-galactosyl transfer to glycoprotein using bovine β-(1 → 4)-galactosyltransferase and UDP-6-deoxy-d-galactose
  作者：Yasuhiro Kajihara、Tsuyoshi Endo、Hiroyuki Ogasawara、Hisashi Kodama、Hironobu Hashimoto

  DOI：10.1016/0008-6215(94)00369-q

  日期：1995.4

  UDP-6-Deoxy-D-galactose and UDP-6-deoxy-6-fluoro-D-galactose were synthesized and their transfer to 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine) by beta-(1 --> 4)galactosyltransferase was examined. The transfer rates of 6-deoxy-D-galactose and 6-deoxy-6-fluoro-D-galactose were 1.3 and 0.2% of that of D-galactosyl transfer, respectively. The 2-acetamido-4-O-(6-deoxy-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranose (6'-deoxy-N-acetyllactosamine) and methyl 2-acetamido-4-O-(6-deoxy-6-fluoro-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranoside (6'-deoxy-6'-fluoro-N-acetyllactosamine) were synthesized enzymatically in 30 and 59% yields, respectively. Further, 6-deoxy-D-galactose could be completely transferred to N-linked type biantennary oligosaccharides having two N-acetyl-D-glucosaminyl residues at the nonreducing end to give the corresponding penta- and hepta-saccharides in 55 and 57% yields, respectively. An assay of 6-deoxy-D-galactosyl transfer using asialo agalacto alpha(1)-acid glycoprotein as an acceptor suggested that 6-deoxy-D-galactose was transferred to about 30% of the N-acetyl-D-glucosaminyl residues in the N-linked oligosaccharides of the glycoprotein.