N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester | 248927-81-3

• 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-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester
• CAS: 248927-81-3
• 化学式: C₆₄H₇₀N₂O₁₅
• 分子量: 1107.26
• InChiKey: CZNSPVNLCAUNAT-QKGAMYAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  81.0
• 可旋转键数：
  26.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  208.03
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane 、 N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以86%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester
  参考文献：
  名称：

  A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis

  摘要：

  In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00649-3
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester 在 三氟乙酸 作用下， 生成 N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester
  参考文献：
  名称：

  A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis

  摘要：

  In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00649-3