Nα-fluorenylmethoxycarbonyl-Nω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine allyl ester | 905456-86-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Nα-fluorenylmethoxycarbonyl-Nω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine allyl ester
• 英文别名: N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine allyl ester
• CAS: 905456-86-2
• 化学式: C₇₆H₈₃N₃O₁₉
• 分子量: 1342.5
• InChiKey: WPOYDAIVVUHENU-VWEAFVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.48
• 重原子数：
  98.0
• 可旋转键数：
  31.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  275.82
• 氢给体数：
  6.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  Nα-fluorenylmethoxycarbonyl-Nω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine allyl ester 在 四(三苯基膦)钯 N-甲基苯胺 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine
  参考文献：
  名称：

  Highly regioselective synthesis of a 3-O-sulfonated arabino Lewisa asparagine building block suitable for glycopeptide synthesis

  摘要：

  Using the stannylene method, the trisaccharide 2-acetamido-3-O-[6-0-benzyl-beta-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-beta-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl azide was regioselectively sulfonated and, after reduction of the anomeric azide, coupled to Fmoc alpha-allyl aspartate. After Pd(0)-catalyzed deallylation, the sulfatyl Lewis(a) asparagine building block was obtained, suitable for solid-phase glycopeptide synthesis applying the fluoride labile PTMSEL linker system. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.003
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide 在 镍 甲醇 、 三乙基硅烷 、 N-羟基-7-氮杂苯并三氮唑 、 三氟甲磺酸 、 3 A molecular sieve 、 4 A molecular sieve 、 四丁基溴化铵 、 氢气 、 sodium 、 氰化汞 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 copper(ll) bromide 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 334.0h， 生成 Nα-fluorenylmethoxycarbonyl-Nω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine allyl ester
  参考文献：
  名称：

  Highly regioselective synthesis of a 3-O-sulfonated arabino Lewisa asparagine building block suitable for glycopeptide synthesis

  摘要：

  Using the stannylene method, the trisaccharide 2-acetamido-3-O-[6-0-benzyl-beta-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-beta-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl azide was regioselectively sulfonated and, after reduction of the anomeric azide, coupled to Fmoc alpha-allyl aspartate. After Pd(0)-catalyzed deallylation, the sulfatyl Lewis(a) asparagine building block was obtained, suitable for solid-phase glycopeptide synthesis applying the fluoride labile PTMSEL linker system. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.003