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 | 905456-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 905456-80-6
• 化学式: C₅₄H₆₄N₂O₁₇S
• 分子量: 1045.17
• InChiKey: ZTYFFMWJMZFFAC-OYYNFKNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  74.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  251.48
• 氢给体数：
  5.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  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 、 (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid 在 N-羟基-7-氮杂苯并三氮唑 、 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-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以66%的产率得到N^α-fluorenylmethoxycarbonyl-N^ω-(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)-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
• 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 、 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 、 二正丁基氧化锡 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 异丙醇 为溶剂， 反应 332.5h， 生成 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