phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucoside | 124595-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucoside
• 英文别名: phenyl 2,3,4-tri-O-aceyl-1-thio-β-D-glucopyranoside；Phenyl 2,3,4-tri-O-acetyl-1-thio-D-glucopyranoside；phenyl 2,3,4-tri-O-Ac-β-D-thioglucopyranoside；phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 124595-24-0
• 化学式: C₁₈H₂₂O₈S
• 分子量: 398.434
• InChiKey: DIVGTOCRLJGASM-SFFUCWETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucoside 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 phenyl 2,3,4-tri-O-acetyl-6-S-acetyl-1,6-dithio-β-D-glucoside
  参考文献：
  名称：

  从糖苷水解酶到硫糖寡糖：硫糖苷的合成

  摘要：

  用适当的糖基供体和糖苷水解酶或糖合酶处理各种含活性硫醇基的糖基受体，都不能产生任何硫糖苷，只能形成O-糖基化产物。然而，当使用硫代糖基寡糖酶来介导受体和供体之间的反应时，形成了硫代糖苷。实际上，在C3，C4或C6具有巯基的吡喃糖受体（但没有C2）均能够转化为硫糖苷。给出了有关各种过程机制的一些评论。

  DOI：

  10.1016/j.tetasy.2004.12.004
• 作为产物：
  描述：

  苯硫酚 在 三氟化硼乙醚 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 58.0h， 生成 phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucoside
  参考文献：
  名称：

  Access to Galectin-3 Inhibitors from Chemoenzymatic Synthons

  摘要：

  Chemoenzymatic strategies are useful for providing both regio- and stereoselective access to bioactive oligosaccharides. We show herein that a glycosynthase mutant of a Thermus thermophilus α-glycosidase can react with unnatural glycosides such as 6-azido-6-deoxy-d-glucose/glucosamine to lead to β-d-galactopyranosyl-(1→3)-d-glucopyranoside or β-d-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-d-glucopyranoside derivatives bearing a unique azide function. Taking advantage of the orthogonality between the azide and the hydroxyl functional groups, the former was next selectively reacted to give rise to a library of galectin-3 inhibitors. Combining enzyme substrate promiscuity and bioorthogonality thus appears as a powerful strategy to rapidly access to sugar-based ligands.

  DOI：

  10.1021/acs.joc.0c01927

文献信息

• Selective removal of anomeric O-acetate groups in carbohydrates using HClO4–SiO2
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2006.03.050

  日期：2006.5

  A convenient methodology has been developed for the selective removal of the anomeric acyl group of carbohydrate derivatives using HClO4–SiO2 under acidic reaction conditions. Anomeric benzoyl groups can also be removed selectively following similar reaction conditions. The yields were excellent in all cases.

  已经开发了一种方便的方法，用于在酸性反应条件下使用HClO 4 -SiO 2选择性除去碳水化合物衍生物的异头酰基。在类似的反应条件下，也可以选择性地除去端基的苯甲酰基。在所有情况下，收率都非常好。
• A catalytic Koenigs-Knorr glycosylation based on acceptor activation with In(NTf2)3
  作者：Changwei Li、Haijing Liang、Zhan-xin Zhang、Zhaoyan Wang、Lan Yu、Huanxiang Liu、Fengli An、Shaohua Wang、Lixia Ma、Weihua Xue

  DOI：10.1016/j.tet.2018.05.080

  日期：2018.7

  important for gaining better insight into biological processes of significance to medicinal chemistry. Herein, we describe an In(NTf2)3 -catalyzed Koenigs-Knorr glycosylation based on the activation of an alcoholic hydroxyl group. A catalytic amount of In(NTf2)3 enables effective glycosylation of diverse alcohols with peracylated aldosyl bromides as donors, leading to the stereoselective formation of a series

  有效的糖基化方法的开发对于更好地了解对药物化学具有重要意义的生物学过程至关重要。在本文中，我们描述了基于醇羟基的活化的In（NTf 2）3催化的Koenigs-Knorr糖基化。催化量的In（NTf 2）3使用过酰基化的醛糖基溴作为供体，可以使各种醇类有效糖基化，从而以令人满意的收率立体选择性地形成一系列糖苷。该方案的特点是反应条件温和，官能团耐受性好，同时不需要任何添加剂。而且，这种转化的潜在效用通过重要的药用相关生物分子合成的便捷合成得到了证明。
• Efficient glycosylation with glycosyl ortho-allylbenzoates as donors
  作者：Haijing Liang、Lixia Ma、Changwei Li、Qiang Peng、Zhaoyan Wang、Zhan-xin Zhang、Lan Yu、Huanxiang Liu、Fengli An、Weihua Xue

  DOI：10.1016/j.tetlet.2018.11.061

  日期：2019.1

  Glycosylation reactions are significant as they provide access to model compounds that are useful for elucidating biochemical pathways. Herein, we describe the development of glycosyl ortho-alkynylbenzoates as novel, bench-top stable, and readily available glycosyl donors. Glycosylation is promoted by inexpensive trimethylsilyl triflate (TMSOTf) in combination with N-iodosuccinimide (NIS) under mild

  糖基化反应很重要，因为它们提供了可用于阐明生化途径的模型化合物的途径。在本文中，我们描述了糖基邻炔基苯甲酸酯作为新型，台式稳定且易于获得的糖基供体的发展。廉价的三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）与N-碘代琥珀酰亚胺（NIS）组合可在温和的反应条件下促进糖基化。因此，新型糖基供体是合成糖苷的有前途的试剂。
• A novel strategy for regio- and stereo-control in glycosylation reactions: template-directed cyclo-glycosylation of monosaccharides
  作者：Serafín Valverde、Ana M. Gómez、Amparo Hernández、Bernardo Herradón、J. Cristóbal López

  DOI：10.1039/c39950002005

  日期：——

  Intramolecular glycosylation of several glucose derived glycosyl donor and acceptors that are linked, at O-6 and O-2 respectively, to a bifunctional spacer results in the regio- and stereo-controlled formation of 13-membered macrocyclic glycosides which can be easily converted to disaccharides.

  几个葡萄糖衍生的糖基供体和受体的分子内糖基化，分别在O-6和O-2处与双功能间隔基连接，导致13位大环糖苷的区域和立体控制形成，可以很容易地转化为二糖。
• One-pot sequential glycosylation: A new method for the synthesis of oligosaccharides
  作者：Haruo Yamada、Takeo Harada、Hiroshi Miyazaki、Takashi Takahashi

  DOI：10.1016/s0040-4039(00)76718-9

  日期：1994.6

  Sequential one-pot glycosylations among various glycosidic donors (glycosyl bromide, glycosyl trichloroimidate, glycosyl fluoride), a β-thiophenyl glycoside derivative and a α-methyl glycoside derivative have been attempted to give the corresponding trisaccharides.

  已经尝试了各种糖苷供体（糖基溴，糖基三氯亚氨酸酯，糖基氟化物），β-硫代苯基糖苷衍生物和α-甲基糖苷衍生物之间的顺序一锅糖基化，以给出相应的三糖。