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 | 905456-87-3

• 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: 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
• 英文别名: (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-6-(phenylmethoxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5-[(2S,3S,4R,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyoxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
• CAS: 905456-87-3
• 化学式: C₇₃H₇₉N₃O₁₉
• 分子量: 1302.44
• InChiKey: KGTDAHZPXYTOAD-BYYONZAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  95
• 可旋转键数：
  30
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  287
• 氢给体数：
  7
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  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 、 Fmoc-O-苄基-L-丝氨酸 、 芴甲氧羰基-L-谷氨酸-Γ-苄脂 、 芴甲氧羰基-天冬氨酸-β苄脂 、 alkaline earth salt of/the/ methylsulfuric acid 以43%的产率得到
  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：

  1,2,3,4-tetra-O-acetyl-6-O-benzyl-D-galactopyranose 在 四(三苯基膦)钯 、 镍 甲醇 、 三乙基硅烷 、 N-羟基-7-氮杂苯并三氮唑 、 bismuth(III) bromide 、 三甲基溴硅烷 、 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-) 、 N-甲基苯胺 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 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 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

文献信息

• Highly regioselective synthesis of a 3-O-sulfonated arabino Lewisa asparagine building block suitable for glycopeptide synthesis
  作者：Alexander Rösch、Horst Kunz

  DOI：10.1016/j.carres.2006.03.003

  日期：2006.7

  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.