2-acetamido-3-O-[6-O-benzyl-3-O-sulfatyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide | 905456-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3-O-[6-O-benzyl-3-O-sulfatyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide
• 英文别名: Bn(-6)Gal3S(b1-3)[Bn(-2)[Bn(-3)][Bn(-4)]D-Ara(b1-4)][Bn(-6)]GlcNAc(b)-N3；[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-azido-6-(phenylmethoxymethyl)-5-[(2S,3S,4R,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyoxan-4-yl]oxy-3,5-dihydroxy-6-(phenylmethoxymethyl)oxan-4-yl] hydrogen sulfate
• CAS: 905456-83-9
• 化学式: C₅₄H₆₂N₄O₁₇S
• 分子量: 1071.17
• InChiKey: CIFUXHZUQGFZOT-OYYNFKNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  76
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  248
• 氢给体数：
  4
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-acetamido-3-O-[6-O-benzyl-3-O-sulfatyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide 在 镍 氢气 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.5h， 以100%的产率得到Sulfuric acid mono-{(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5S,6R)-3-acetylamino-2-amino-6-benzyloxymethyl-5-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-3,5-dihydroxy-tetrahydro-pyran-4-yl} 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
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-benzyl-D-galactopyranose 在 甲醇 、 三乙基硅烷 、 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 、 sodium 、 氰化汞 、 二正丁基氧化锡 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 329.0h， 生成 2-acetamido-3-O-[6-O-benzyl-3-O-sulfatyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide
  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.