O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose | 104139-78-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose
• CAS: 104139-78-8
• 化学式: C₄₀H₄₂ClN₃O₁₅
• 分子量: 840.238
• InChiKey: PZGHNBMJINEGRO-LJIXZZMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  226.41
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 溴化钛(IV) 、 硫脲 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 22.17h， 生成 methyl O-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of methyl glycoside derivatives of tri- and penta-saccharides related to the antithrombin III-binding sequence of heparin, employing cellobiose as a key starting-material

  摘要：

  Two key synthons for the title pentasaccharide derivative, methyl O-(methyl 2-O-benzoyl-3-O-benzyl-alpha-L-idopyranosyluronate)-(1----4)-6-O-acetyl- 2-azido - 3-O- benzyl-2-deoxy-beta-D-glucopyranoside and O-(methyl 2,3-di-O-benzyl-4-O- chloroacetyl-beta-D-glucopyranosyluronate)-(1----4)-3,6-di-O-acetyl-2-az ido-2- deoxy-alpha-D- glucopyranosyl bromide, were prepared from a common starting material, cellobiose. They were coupled to give a tetrasaccharide derivative that underwent O-dechloroacetylation to the corresponding glycosyl acceptor. Its condensation with the known 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide afforded a 77% yield of suitably protected pentasaccharide, methyl O-(6-O- acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1----4)- O- (methyl 2,3- di-O-benzyl-beta-D-glucopyranosyluronate)-(1----4)-O-(3,6-di-O-acetyl-2- azido-2 - deoxy-alpha-D-glucopyranosyl)-(1----4)-O-(methyl 2-O-benzoyl-3-O-benzyl-alpha-L- idopyranosyluronate)- (1----4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-beta-D-glucopyranoside. Sequential deprotection and sulfation gave the decasodium salt of methyl O-(2- deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1----4)-O-(be ta-D- glucopyranosyl-uronic acid)-(1----4)-O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-gluco pyranosyl)- (1----4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1----4)-2-deoxy-2- sulfamido-6-O- sulfo-beta-D-glucopyranoside (3). In a similar way, the trisaccharide derivative, the hexasodium salt of methyl O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D- glucopyranosyl)- (1----4)-O-(beta-D-glucopyranosyluronic acid)-(1----4)-2-deoxy-2-sulfamido-3,6- di-O- sulfo-alpha-D-glucopyranoside (4) was synthesized from methyl O-(6-O-acetyl-2- azido- 3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1----4)-O-(methyl 2,3-di-O- benzyl-beta- D-glucopyranosyluronate)-3,6-di-O-acetyl-2-azido-2-deoxy-alpha-D- glucopyranoside. The pentasaccharide 3 binds strongly to antithrombin III with an association constant almost equivalent to that of high-affinity heparin, but the trisaccharide 4 appears not to bind.

  DOI：

  10.1016/s0008-6215(00)90842-5
• 作为产物：
  描述：

  O-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  以纤维二糖为主要原料合成对抗凝血酶III具有高亲和力的肝素五糖片段

  摘要：

  建立了纤维二糖的区域和立体选择性修饰和转化的方法，并将其用于对抗凝血酶III具有高亲和力的肝素五糖片段的全合成。

  DOI：

  10.1016/s0040-4039(00)84054-x