{(2S,3R,4R,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester | 273749-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(2S,3R,4R,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester
• CAS: 273749-70-5
• 化学式: C₃₈H₄₆Cl₃NO₁₃
• 分子量: 831.141
• InChiKey: IQAFPWREJMJARD-CLVYNTRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  55.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172.86
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  {(2S,3R,4R,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester 在 palladium dihydroxide 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 四丁基溴化铵 、 氢气 、 sodium 、 对甲苯磺酸 、 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， -30.0~20.0 ℃ 、413.7 kPa 条件下， 反应 113.25h， 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 2,3-di-O-benzyl-4,6-O-(4-methoxybenzyl)-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 guanidinium nitrate 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 {(2S,3R,4R,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester
  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