N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4-tri-O-benzyl-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 | 1192143-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4-tri-O-benzyl-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
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-2-[(2S)-2-[[9H-fluoren-9-ylmethoxy(hydroxy)methylidene]amino]-3-oxo-3-phenacyloxypropoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-5-[(2S,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]ethanimidic acid
• CAS: 1192143-02-4
• 化学式: C₁₀₂H₁₀₄N₂O₂₁
• 分子量: 1693.95
• InChiKey: PYTLQXWRBDMDSB-QWMHKHCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  125
• 可旋转键数：
  44
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  267
• 氢给体数：
  3
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4-tri-O-benzyl-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 三甲基铵三氧化硫共聚物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以76%的产率得到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
  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
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4-tri-O-benzyl-6-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]-L-serine phenacyl ester 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4-tri-O-benzyl-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
  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