phenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside | 213882-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5S)-3,4-dibenzoyloxy-5-phenylsulfanyloxolan-2-yl]ethyl] benzoate
• CAS: 213882-36-1
• 化学式: C₄₀H₃₂O₉S
• 分子量: 688.755
• InChiKey: NMBTUTIBFYZSBE-OJECGNTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside 在 N-碘代糖精 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以82%的产率得到2,3,5,6-tetra-O-benzoyl-D-galactofuranose
  参考文献：
  名称：

  Mild and Efficient Hydrolysis of Thioglycosides to Glycosyl Hemiacetals Using N-Iodosaccharin

  摘要：

  已开发出一种便捷的方法，利用N-碘代糖精在无需任何共活化剂的条件下对硫苷进行温和水解，生成相应的半缩醛。在反应条件下，大多数用于糖类保护基操作的功能团保持不受影响。

  DOI：

  10.1055/s-2007-977412
• 作为产物：
  描述：

  (R)-1-((2S,3R,4S,5S)-3,4-bis(benzoyloxy)-5-(2,2,2-trichloro-1-iminoethyl)tetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate 、 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 phenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  Total synthesis of fuzinoside

  摘要：

  The first total syntheses of fuzinoside (1b) were achieved from o-galactose through two strategies (BCA and ABC) in 11 (total yield: 5.0%) and 15 (total yield: 3.7%) steps, respectively. Comparison of NMR data of synthetic compound 1b and those of the fuzinoside isolated from the lateral roots of Aconitum carmicaelii suggests that the structure reported in the literature(1,2) might not be accurate. The synthetic fuzinoside (1b) exhibited moderate cardiac activity in the isolated bullfrog heart assay. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.069

文献信息

• One-pot synthesis of branched oligosaccharides by use of galacto- and mannopyranosyl thioglycoside diols as key glycosylating agents
  作者：Xing-Yong Liang、Qiang-Wei Liu、Hua-Chao Bin、Jin-Song Yang

  DOI：10.1039/c3ob40421h

  日期：——

  one-pot synthesis of three fully protected oligosaccharides 22, 36, and 50 with di-branched structures by employing D-galacto- and mannopyranosyl thioglycoside diols as central glycosylating agents. After global deprotection, they were converted respectively into the 3-aminopropyl linker-containing free oligosaccharide fragments 14, 24, and 38 structurally related to cell wall oligosaccharides from Atractylodes

  我们描述在本文中的高效的四组分一锅合成的三个完全受保护的低聚糖22，36，和50与二支化结构通过采用d -galacto-和吡喃甘露糖基硫代糖苷二醇中央糖基化剂。完全脱保护后，将它们分别转化成3-氨基丙基含有接头-自由寡糖片段14，24，和38结构上与细胞壁寡糖从苍术DC，海洋真菌Lineolata rhizophorae和致病结核分枝杆菌。异头碳原子上的3-氨基丙基接头可使这些合成的低聚物与合适的蛋白质载体缀合。
• 6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity
  作者：Jeane Vaugenot、Abderrafek El Harras、Olivier Tasseau、Rémi Marchal、Laurent Legentil、Boris Le Guennic、Thierry Benvegnu、Vincent Ferrières

  DOI：10.1039/c9ob02596k

  日期：——

  Standard glycosylation of unprotected 6-fluorogalactofuranoside turned to three competitive reactions and afforded difuranosides able to impact growth of Leishmania tarentolae.

  不保护的6-氟半乳糖苷的标准糖基化转化为三个竞争反应，并得到能够影响蜥蜴利什曼原虫生长的二氧杂环糖苷。
• A NEW APPROACH TO A DISACCHARIDIC HAPTEN CONTAINING A GALACTOFURANOSYL ENTITY
  作者：Vincent Ferrières、Myriam Roussel、Muriel Gelin、Daniel Plusquellec

  DOI：10.1081/car-100108662

  日期：2001.12.31

  A short synthetic entry into the disaccharidic hapten beta-D-Galf-(1-->3)-alpha-D-Manp-O(CH2)(8)CO2Me containing a galactofuranosyl entity at the non-reducing part is described. The synthetic scheme was designed in such a way that each required building block could be obtained by minimizing the number of chemical and purification steps. Indeed, compound 8 was obtained according to a four step-one pot preparation.
• Unexpected fluorous solvent effect on oxidation of 1-thioglycosides
  作者：Khalid Misbahi、Morgane Lardic、Vincent Ferrières、Nicolas Noiret、Abdelali Kerbal、Daniel Plusquellec

  DOI：10.1016/s0957-4166(01)00437-2

  日期：2001.9

  Oxidation of various 1-thioglycopyrano- and furanosides with H2O2/Ac2O/SiO2 was performed in CH2Cl2/aprotic perfluorinated solvent mixtures (100:0 to 1:19, v/v). Reactions appeared much faster at a solvent ratio of 1:1 without significant over-oxidation to sulfones and modification of diastereoselectivity. Nevertheless, the nature of both the glycosyl moiety and the protecting group influenced the (S-S):(R-S) product ratio. (C) 2001 Published by Elsevier Science Ltd.
• Influence of Silyl Protections on the Anomeric Reactivity of Galactofuranosyl Thioglycosides and Application of the Silylated Thiogalactofuranosides to One-Pot Synthesis of Diverse β-<scp>d</scp>-Oligogalactofuranosides
  作者：Shuai Wang、Xue Meng、Wei Huang、Jin-Song Yang

  DOI：10.1021/jo5018684

  日期：2014.11.7

  We describe in this paper the tuning effect of silyl protecting groups on the donor reactivity of galactofuranosyl phenyl thioglycosides. Silyl ethers on the galactofuranose ring are found to have an arming effect on the glycosylation reactivity, but the cyclic 3,5-acetal protecting group decreases the reactivity. The reactive phenyl 2,6-di-O-Bz-3,5-di-O-TBS-1-thio-beta-d-galactofuranoside 3 is proved to be a useful glycosyl building block. By taking advantage of this donor, we achieved the highly efficient one-pot solution-phase assembly of a panel of beta-d-galactofuranosyl tri- and tetrasaccharides possessing diverse glycosidic linkages.