N-[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-2-phenyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide | 273749-57-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-2-phenyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 273749-57-8
• 化学式: C₄₂H₅₃NO₁₆
• 分子量: 827.88
• InChiKey: VREFUYXULPBNJS-BQNCBVFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  59
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  223
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N-[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-2-phenyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide 在 palladium dihydroxide 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 四丁基溴化铵 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 60.0h， 生成 O-(β-D-glucopyranosyluronic acid)-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-β-D-methyl-glucopyranosiduronic acid
  参考文献：
  名称：

  Synthesis of Two Hyaluronan Trisaccharides

  摘要：

  The synthesis of two hyaluronan trisaccharides, methyl O(beta-D-glucopyranosyluronic acid)-(1,3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1,4)-O-beta-D-glucopyranosiduronic acid and methyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1,4)-O-beta-D-glycopyranosyluronic acid)-(1,3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranoside are described. Construction of the target molecules was achieved though a combination of the phenyl sulfoxide and trichloroacetimidate glycosylation methodologies. This is the first report on the synthesis of the beta-methyl derivatives, which represent the smallest fragments that incorporate all the structural features of polymeric hyaluronan.

  DOI：

  10.1021/ol0057075
• 作为产物：
  描述：

  methyl O-(4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 镉 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 52.5h， 生成 N-[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-2-phenyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
  参考文献：
  名称：

  Synthesis of Two Hyaluronan Trisaccharides

  摘要：

  The synthesis of two hyaluronan trisaccharides, methyl O(beta-D-glucopyranosyluronic acid)-(1,3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1,4)-O-beta-D-glucopyranosiduronic acid and methyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1,4)-O-beta-D-glycopyranosyluronic acid)-(1,3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranoside are described. Construction of the target molecules was achieved though a combination of the phenyl sulfoxide and trichloroacetimidate glycosylation methodologies. This is the first report on the synthesis of the beta-methyl derivatives, which represent the smallest fragments that incorporate all the structural features of polymeric hyaluronan.

  DOI：

  10.1021/ol0057075

文献信息

• Synthesis of Two Hyaluronan Trisaccharides
  作者：Bryan K. S. Yeung、Daniel C. Hill、Maria Janicka、Peter A. Petillo

  DOI：10.1021/ol0057075

  日期：2000.5.1

  The synthesis of two hyaluronan trisaccharides, methyl O(beta-D-glucopyranosyluronic acid)-(1,3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1,4)-O-beta-D-glucopyranosiduronic acid and methyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1,4)-O-beta-D-glycopyranosyluronic acid)-(1,3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranoside are described. Construction of the target molecules was achieved though a combination of the phenyl sulfoxide and trichloroacetimidate glycosylation methodologies. This is the first report on the synthesis of the beta-methyl derivatives, which represent the smallest fragments that incorporate all the structural features of polymeric hyaluronan.