| 1192143-13-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1192143-13-7
• 化学式: C₄₆H₅₆N₂O₂₄S
• 分子量: 1053.02
• InChiKey: CAQAXVBMXVJQPU-CWBJURRVSA-N

反应信息

• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4-tri-O-benzyl-6-O-sulfo-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]-L-serine phenacyl ester 在 二甲基硫 、 间甲酚 、 三氟乙酸 、 三氟甲磺酸 作用下， 反应 7.0h， 生成 、
  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