[(1R,3R,5S,7R,8S,9R,11R)-5-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-6-azido-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(chloromethyl)-11-phenyl-2,4,6,10,12-pentaoxatricyclo[7.4.0.03,7]tridecan-8-yl] acetate | 1132975-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,3R,5S,7R,8S,9R,11R)-5-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-6-azido-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(chloromethyl)-11-phenyl-2,4,6,10,12-pentaoxatricyclo[7.4.0.03,7]tridecan-8-yl] acetate
• CAS: 1132975-34-8
• 化学式: C₇₃H₆₈ClN₅O₁₉
• 分子量: 1354.82
• InChiKey: QORQDWSIRJJEJF-BKYGVDTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  98
• 可旋转键数：
  25
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  235
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  [(1R,3R,5S,7R,8S,9R,11R)-5-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-6-azido-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(chloromethyl)-11-phenyl-2,4,6,10,12-pentaoxatricyclo[7.4.0.03,7]tridecan-8-yl] acetate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到O-(3-O-acetyl-4,6-O-benzylidene-2-chloroacetyl-β-D-glucopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide
  参考文献：
  名称：

  Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type

  摘要：

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.

  DOI：

  10.1021/jo900016j
• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 [(1R,3R,5S,7R,8S,9R,11R)-5-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-6-azido-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(chloromethyl)-11-phenyl-2,4,6,10,12-pentaoxatricyclo[7.4.0.03,7]tridecan-8-yl] acetate
  参考文献：
  名称：

  Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type

  摘要：

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.

  DOI：

  10.1021/jo900016j