S-phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-thiomannopyranoside | 848397-71-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-thiomannopyranoside
• CAS: 848397-71-7
• 化学式: C₃₃H₃₂O₇S₂
• 分子量: 604.745
• InChiKey: JSBJJJMLBBYEFS-HOEDGPACSA-N

物化性质

• 沸点：
  747.4±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  S-phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-thiomannopyranoside 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2R,4aR,6R,7R,8S,8aR)-8-Benzyloxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylamine
  参考文献：
  名称：

  Glycosyl azides of sugar 2-sulfonic acids

  摘要：

  Phenyl and trityl 2-O-stilfonyl-1-thio-alpha-D-manno- and beta-D-glucopyranosides were reacted with sodium azide to yield 2-S-phenyl or 2-S-trityl-D-gluco- and D-mannopyranosyl azides, respectively. Usually, both anomers were formed in approximately equal amounts and formation of glycals was also observed in some cases. The product distribution of these reactions depends on the nature of the aglycone, the applied reagent and also on the solvent. These results can be rationalised by the intermediacy of episulfonium as well as oxocarbenium ions. Oxidation of the 2-S-trityl-alpha-D-glycopyranosyl or alpha-D-mannopyranosyl azides by Oxone (R). gave sodium 2-sulfonato-alpha-D-gluco- and alpha-D-mannopyranosyl azides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.112
• 作为产物：
  描述：

  对甲苯磺酰氯 、 (2R,4AR,6R,7S,8R,8AR)-8-(苄氧基)-2-苯基-6-(苯硫基)六氢吡喃并[3,2-D][1,3]二氧杂环己烯-7-醇 在 silver nitrate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以81%的产率得到S-phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-thiomannopyranoside
  参考文献：
  名称：

  Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates

  摘要：

  A series of D-mannopyranosyl and L-rhamnopyranosyl thioglycosides; protected with electron-withdrawing non-participating protecting groups on O-2 have been prepared and investigated for their potential as beta-glycosyl donors. Both alpha- and beta-thioglycosides were investigated and the latter preferred on the grounds of enhanced stability at room temperature. A 2-O-nitro-L-rhamnosyl fluoride was also prepared and investigated. Moderate beta-selectivities were observed with some of these donors. With the more powerfully electron-withdrawing groups reduced donor reactivity leads to a requirement for higher reaction temperatures and reduced selectivities. Decomposition temperatures of the intermediate glycosyl triflates were determined by variable temperature NMR spectroscopy and generally correlate with the disarming propensity of the protecting group system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.032