phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-thio-β-D-glucopyranoside | 1610714-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-thio-β-D-glucopyranoside
• CAS: 1610714-25-4
• 化学式: C₄₇H₅₂O₁₄S
• 分子量: 872.987
• InChiKey: WCBDDGJSHIEWFS-CERNNEFUSA-N

物化性质

• 沸点：
  861.4±65.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 、 (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 在 三乙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-thio-β-D-glucopyranoside
  参考文献：
  名称：

  HClO4–silica-catalysed regioselective opening of benzylidene acetals and its application towards regioselective HO-4 glycosylation of benzylidene acetals in one-pot

  摘要：

  Here we report a high-yielding method for the regioselective reductive ring opening of 4,6-O-benzylidene acetals of hexapyranosides using inexpensive and robust HClO4-SiO2 as the acidic catalyst and triethyl-silane as the hydride donor. Under the optimized condition, gluco-and mannopyranosides give the respective 6-O-benzyl derivative in good to excellent yields while the corresponding galactopyranoside gives the corresponding 6-O-benzyl derivative in lower yield. As the optimized condition involves acidic catalyst, we also successfully developed further application of the present method for the tandem regioselective opening and glycosylation in one-pot. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.01.011