(2R,3R,4S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-phenylsulfanyloxolane | 153481-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-phenylsulfanyloxolane
• CAS: 153481-95-9
• 化学式: C₃₂H₃₂O₄S
• 分子量: 512.67
• InChiKey: XSIFTEPGOQOODG-WIDWRGJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-phenylsulfanyloxolane 在 IF₅-pyridine-HF 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以77%的产率得到2,3,5-tri-O-benzyl-D-arabinofuranosyl fluoride
  参考文献：
  名称：

  Synthesis of glycosyl fluorides from (phenylthio)glycosides using IF5–pyridine–HF

  摘要：

  IF5-pyridine-HF, an air- and moisture-stable fluorinating reagent, was applied to the synthesis of glycosyl fluorides from (phenylthio) glycosides. Common protecting groups of alcohol and diol can tolerate the reaction conditions performed, and therefore, the present method is applicable to the synthesis of various glycosyl fluorides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.08.005
• 作为产物：
  描述：

  锡烷,二丁基二(苯基硫代)- 、 1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 在 dibutylstannanediyl bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以100%的产率得到(2R,3R,4S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-phenylsulfanyloxolane
  参考文献：
  名称：

  硫代锡烷的活化和合成应用。合成硫代和硒代糖苷的新方法

  摘要：

  在催化量的Bu 2 Sn（OTf）2的存在下将硫代锡烷暴露于乙酰基或甲基糖苷可提供高收率的硫代糖苷。通过使用硒炔诺酮以类似的方式实现硒代糖苷化。

  DOI：

  10.1016/0040-4039(92)88060-i

文献信息

• Stereoselective Synthesis of 1,2-<i>cis</i>-<i>N</i>-Glycosides by the<i>N</i>-Bromosuccinimide Promoted Reaction of Thioglycosides with Silylated Pyrimidme Bases
  作者：Hideyuki Sugimura、Ikuyo Muramoto、Tadashi Nakamura、Kenji Osumi

  DOI：10.1246/cl.1993.169

  日期：1993.1

  The coupling of O-benzylated 1-thioglycosides, derived from d-glucose, d-mannose, d-ribose, d-xylose, and d-arabinose, with silylated pyrimidme bases by activation with N-bromosuccinimide uniformly afforded the corresponding 1,2-cis-N-glycosides with good selectivity.

  通过N-溴代琥珀酰亚胺活化，将源自d-葡萄糖、d-甘露糖、d-核糖、d-木糖和d-阿拉伯糖的O-苄基1-硫代糖苷与硅烷化的嘧啶碱结合，可以均匀地得到具有良好选择性的相应1,2-顺式-N-糖苷。
• Influence of 4′-<i>O</i>-Glycoside Constitution and Configuration on Ribosomal Selectivity of Paromomycin
  作者：Takahiko Matsushita、Weiwei Chen、Reda Juskeviciene、Youjin Teo、Dimitri Shcherbakov、Andrea Vasella、Erik C. Böttger、David Crich

  DOI：10.1021/jacs.5b02248

  日期：2015.6.24

  A series of 20 4'-O-glycosides of the aminoglycoside antibiotic paromomycin were syntheized and evaluated for their ability to inhibit protein synthesis by bacterial, mitochondrial and cytosolic ribosomes. Target selectivity, i.e., inhibition of the bacterial ribosome over eukaryotic mitochondrial and cytosolic ribosomes, which is predictive of antibacterial activity with reduced ototoxicity and systemic toxicity, was greater for the equatorial than for the axial pyranosides, and greater for the D-pentopyranosides than for the L-pentopyranosides and D-hexopyranosides. In particular, 4'-O-,beta-D-xylopyranosyl paromomycin shows antibacterioribosomal activity comparable to that of paromomycin, but is significantly more selective showing considerably reduced affinity for the cytosolic ribosome and for the A1555G mutant mitochondrial ribosome associated with hypersusceptibility to drug-induced. ototoxicity. Compound antibacterioribosomal activity correlates with antibacterial activity, and the,ribosomally more active compounds show activity against Escherichia coli, Klebsiella pneumonia, Enterobacter cloacae, Acinetobacter baumannii, and methicillin-resistant Staphylococcus aureus (MRSA). The paromomycin glycosides retain activity against clinical strains of MRSA that are resistant to paromomycin, which is demonstrated to be a consequence of 4'-O-glycosylation blocking the action of 4'-aminoglycoside nucleotidyl transferases by the use Of recombinant E. coli carrying the specific resistance determinant.
• Activation and synthetic applications of thiostannanes. A new method for synthesis of thio- and selenoglycosides
  作者：Tsuneo Sato、Yukihiro Fujita、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/0040-4039(92)88060-i

  日期：1992.1

  Exposure of thiostannane to acetyl or methyl glycosides in the presence of a catalytic amount of Bu2Sn(OTf)2 provides thioglycosides in good yields. Selenoglycosidation is achieved in a like manner by use of selenostannane.

  在催化量的Bu 2 Sn（OTf）2的存在下将硫代锡烷暴露于乙酰基或甲基糖苷可提供高收率的硫代糖苷。通过使用硒炔诺酮以类似的方式实现硒代糖苷化。
• Synthesis of glycosyl fluorides from (phenylthio)glycosides using IF5–pyridine–HF
  作者：Masataka Kunigami、Shoji Hara

  DOI：10.1016/j.carres.2015.08.005

  日期：2015.11

  IF5-pyridine-HF, an air- and moisture-stable fluorinating reagent, was applied to the synthesis of glycosyl fluorides from (phenylthio) glycosides. Common protecting groups of alcohol and diol can tolerate the reaction conditions performed, and therefore, the present method is applicable to the synthesis of various glycosyl fluorides. (C) 2015 Elsevier Ltd. All rights reserved.