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 | 248927-82-4

• 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-[2,3,4,6-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
• 英文别名: prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[dimethyl-[2-(4-nitrophenyl)propan-2-yl]silyl]oxymethyl]-5-hydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 248927-82-4
• 化学式: C₇₅H₈₅N₃O₁₇Si
• 分子量: 1328.6
• InChiKey: MHAARDPLAORMHI-WUEQXJOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.35
• 重原子数：
  96
• 可旋转键数：
  32
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  243
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  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 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 以81%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-aminobenzyl)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 咪唑 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 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