2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride | 1192142-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride
• CAS: 1192142-87-2
• 化学式: C₈₄H₉₀FNO₁₆
• 分子量: 1388.63
• InChiKey: MOELFLNWLGHMGW-CNJUBSFQSA-N

反应信息

• 作为产物：
  描述：

  2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-D-mannopyranose 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到2,4,6-tri-O-benzyl-3-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  Solid-phase synthesis of O-sulfated glycopeptide by the benzyl-protected glycan strategy

  摘要：

  To expand the repertoire of our benzyl-protection strategy for solid-phase glycopeptide synthesis, an C-sulfated glycopeptide was chosen as the synthetic target. Trisaccharyl serine derivatives (Gal beta 1-4-GlcNAc beta 1-2-Many alpha 1-3-Ser) carrying (4-methoxyphenyl)methyl (MPM) groups at either 3-O or 6-O of the Gal residue were prepared through three stereoselective glycosylations. Cleavage of MPM followed by reaction with Me3N center dot SO3 efficiently afforded 3-O- and 6-O-sulfo-glycoserines, respectively. A preliminary debenzylation Study using the sulfated glycoserines revealed that the sulfate groups persisted under 'low-acidity TfOH' conditions, when using a limited amount of TfOH and extending the reaction period. The 3-O-sulfo-glycoserine was then introduced into an icosapeptide modeled after an alpha-dystroglycan fragment by a combination of automated and manual solid-phase peptide synthesis procedures. The synthesized glycopeptide was successfully debenzylated by the low-acidity TfOH cocktail with slight damage to the sulfate functionality. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.080