phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside | 124595-23-9

• 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-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 124595-23-9
• 化学式: C₂₄H₃₆O₈SSi
• 分子量: 512.697
• InChiKey: QJROZZHFAHNRPA-ZQGJOIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside 在 吡啶 、 copper(l) iodide 、 sodium azide 、 glycosynthase E₃₃₈G 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 138.0h， 生成 phenyl β-D-galactopyranosyl(1→3)-6-deoxy-6-[4-(3-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-1-thio-β-D-glucopyranoside
  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
• 作为产物：
  描述：

  苯硫酚 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside
  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

• Facile synthesis of silylated thioglycosides
  作者：Sudhir Nambiar、John F. Daeuble、Ronald J. Doyle、K. Grant Taylor

  DOI：10.1016/s0040-4039(00)99642-4

  日期：1989.1
• Synthesis, biological evaluation and structure-activity relationship studies of hederacolchiside E and its derivatives as potential anti-Alzheimer agents
  作者：Hui-ning Li、Yang Liu、Zuo-peng Zhang、Zhi-peng Wang、Jing-zheng Hao、Feng-ran Li、Zhan-fang Fan、Li-bo Zou、Mao-sheng Cheng

  DOI：10.1016/j.ejmech.2017.11.040

  日期：2018.1

  Inspired by the previously reported neuroprotective activity of hederacolchiside E (1), we synthesized hederacolchiside E for the first time along with eleven of its derivatives. The neuroprotective effects of these compounds were further evaluated against H2O2- and A beta(1-42)-induced injury using cell-based assays. The derivatives showed obvious differences in activity due to structural variations, and two of them exhibited better neuroprotective effects than 1 in the A beta(1-42)-induced injury model. Compound 7 was the most active derivative and had a relatively simple chemical structure. Moreover, 1 and 7 can significantly reduce the release of lactate dehydrogenase (LDH), level of intracellular reactive oxygen species (ROS) and extent of malondialdehyde (MDA) increase resulting from A beta(1-42) treatment, which demonstrated that these kinds of compounds show neuroprotective effects in Alzheimer's disease (AD) models via modulating oxidative stress. Compound 7 could be used as promising lead for the development of a new type of neuroprotective agent against AD. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis of Calocybe indica var. APK2 polysaccharide repeating unit
  作者：Lei Zhang、Xiangming Zhu

  DOI：10.1016/j.carres.2014.04.004

  日期：2014.6

  The first total synthesis of p-methoxyphenyl alpha-L-fucopyranosyl-(1 -> 6)-alpha-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (2) was achieved starting from five monosaccharide building blocks. This structure represents the repeating unit of the polysaccharide isolated from edible mushroom Calocybe indica var. APK2, and was synthesized in high overall yield via a convergent '3+ 2' glycosylation strategy. (C) 2014 Elsevier Ltd. All rights reserved.
• NAMBIAR, SUDHIR;DAEUBLE, JOHN F.;DOYLE, RONALD J.;TAYLOR, K. GRANT, TETRAHEDRON LETT., 30,(1989) N7, C. 2179-2182
  作者：NAMBIAR, SUDHIR、DAEUBLE, JOHN F.、DOYLE, RONALD J.、TAYLOR, K. GRANT

  DOI：——

  日期：——