methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-(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 | 273749-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-(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,3S,4R,5R,6S)-6-[(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-yl]oxy-3,4-diacetyloxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 273749-66-9
• 化学式: C₅₇H₆₅Cl₃N₄O₂₀
• 分子量: 1232.52
• InChiKey: JIMJCNJTOMHIJM-BYQINPTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  84
• 可旋转键数：
  28
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  242
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-(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 硫代乙酸 、 镉 作用下， 以 吡啶 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 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：

  methyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 lithium hydroxide 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 4 A molecular sieve 、 sodium hydride 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-(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