methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 273749-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-6-[[(2R,4aR,6R,7R,8R,8aS)-7-azido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-2-[(4-methoxyphenyl)methoxymethyl]-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 273749-64-7
• 化学式: C₄₂H₄₇N₃O₁₁
• 分子量: 769.849
• InChiKey: UVYGJVMEMFSVDH-PSYSYVOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 四丁基溴化铵 、 硫代乙酸 、 镉 作用下， 以 吡啶 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.83h， 生成 6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic 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：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 3 A molecular sieve 、 4 A molecular sieve 、 sodium 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.33h， 生成 methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  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.