methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(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 | 273749-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(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
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3R,4S,5R,6R)-6-methoxy-2-[(4-methoxyphenyl)methoxymethyl]-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-2-phenyl-7-(2,2,2-trichloroethoxycarbonylamino)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 273749-54-5
• 化学式: C₅₉H₆₈Cl₃NO₂₂
• 分子量: 1249.54
• InChiKey: CPTLNMXUQIQFFM-ZWZYXABOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  85
• 可旋转键数：
  29
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  254
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(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 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 四丁基溴化铵 、 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 52.0h， 生成
  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：

  {(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 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.25h， 生成 methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(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
  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