phenyl-1-thio-β-D-galactofuranoside | 213882-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl-1-thio-β-D-galactofuranoside
• 英文别名: (2S,3R,4R,5S)-2-[(1R)-1,2-dihydroxyethyl]-5-phenylsulfanyloxolane-3,4-diol
• CAS: 213882-41-8
• 化学式: C₁₂H₁₆O₅S
• 分子量: 272.322
• InChiKey: LDAOUZFPDPCBCF-JCIQBVFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl-1-thio-β-D-galactofuranoside 在 吡啶 、 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 phenyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  Influence of Silyl Protections on the Anomeric Reactivity of Galactofuranosyl Thioglycosides and Application of the Silylated Thiogalactofuranosides to One-Pot Synthesis of Diverse β-d-Oligogalactofuranosides

  摘要：

  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.

  DOI：

  10.1021/jo5018684
• 作为产物：
  描述：

  phenyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 phenyl-1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  A General and Diastereoselective Synthesis of 1,2-cis-Hexofuranosides from 1,2-trans-Thiofuranosyl Donors

  摘要：

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1423::aid-ejoc1423>3.0.co;2-9

文献信息

• Improvement of the versatility of an arabinofuranosidase against galactofuranose for the synthesis of galactofuranoconjugates
  作者：Quentin Pavic、Aline Pillot、Olivier Tasseau、Laurent Legentil、Sylvain Tranchimand

  DOI：10.1039/c9ob01162e

  日期：——

  syntheses but the use of galactofuranosidase has not been described yet for the synthesis of galactofuranoconjugates. Interestingly CtAraf51, an α-l-arabinofuranosidase from Ruminiclostridium thermocellum, is able to use aryl- or alkyl-β-d-galactofuranosides as the substrate but with very low efficiency. To allow its use as a synthesis tool, we decided to improve the efficiency of this enzyme toward these non-natural

  半乳糖呋喃共轭物是具有令人感兴趣的生物学特性的稀有化合物。然而，通过传统方法进行的合成是乏味的。如今，糖苷酶经常用于简化此类合成，但尚未描述使用半乳糖呋喃糖苷酶合成半乳糖醛酸缀合物。有趣的是，CtAraf51，一种来自热细单胞菌的α-1-1-阿拉伯呋喃糖苷酶，能够使用芳基-或烷基-β-d-d-半乳糖呋喃糖苷作为底物，但是效率非常低。为了将其用作合成工具，我们决定提高该酶对这些非天然底物的效率。首先，我们确定了三个残基，这些残基可能导致与对硝基苯基-β-d-半乳糖呋喃糖苷的不利相互作用。诱变后 两个突变体的催化效率分别比野生型高四倍和三倍。然后使用乙醇作为模型受体底物在转糖基化反应中评估这两个突变体。在这些条件下，一个突变体的效率要高得多：50％的转化率是野生型的十倍。最终，两个突变体都转化为硫代糖醇：在硫基化反应中，该反应比单个E173A突变体快两倍，在酰化反应中，初始速度提高了四倍。所得突变体合成各种O-，
• A General and Diastereoselective Synthesis of 1,2-cis-Hexofuranosides from 1,2-trans-Thiofuranosyl Donors
  作者：Muriel Gelin、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1423::aid-ejoc1423>3.0.co;2-9

  日期：2000.4
• 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.