methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside | 445397-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside
• CAS: 445397-84-2
• 化学式: C₅₁H₆₂N₂O₁₇
• 分子量: 975.056
• InChiKey: PNWLCFAKBMXKFC-IQZOAJKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  70.0
• 可旋转键数：
  22.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  248.49
• 氢给体数：
  6.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside 在 三甲基氨基磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以65%的产率得到methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sodium sulfonato-β-D-galactopyranosyl)-(1->4)-(sodium 3-O-benzyl-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-4-O-sodium sulfonato-β-D-galactopyranoside
  参考文献：
  名称：

  An access to various sulfation patterns in dermatan sulfate: chemical syntheses of sulfoforms of trisaccharide methyl glycosides

  摘要：

  The syntheses are reported for the first time of alpha-L-IdopA(2)SO(3)-(1-->3)-beta-D-GalpNAc4SO(3)-(1-->4)-alpha-L-IdopA2SO(3)-(1-->OMe), its disulfated analogue alpha-L-IdopA2SO(3)-(1-->3)-beta-D-GalpNAc4SO(3)-(1-->4)-alpha-L-IdopA2SO(3)-(1-->OMe), and of beta-D-GalpNAc4SO(3)-(1-->4)-alpha-L-IdopA2SO(3)-(1-->3)-beta-D-GalpNAc4SO(3)-(1-->OMe), which represent structural fragments of dermatan sulfate, unavailable directly by chemical or enzymatic degradation of the glycosaminoglycan polymer. These molecules were readily obtained from a pair of key disaccharide intermediates, in which the relative difference of stability of the D-GalNAc 4-hydroxy protecting groups (acetate or pivalate) toward saponification conditions allowed access to various sulfoforms from a common precursor. For the preparation of these blocks, the 4-O-pivaloyl-D-galacto moiety was readily obtained through a one-pot stereospecific intramolecular nucleophilic displacement on an easily available 3-O-pivaloyl-D-gluco precursor,and the L-IdoA moiety through selective radical oxidation at C-6 of a L-ido 4,6-diol derivative with oxoammonium salts. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00060-5
• 作为产物：
  描述：

  4-methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-α-L-idopyranoside 在 potassium bromide 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 lithium hydroxide 、 sodium hydroxide 、 calcium hypochlorite 、 ammonium cerium(IV) nitrate 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 双氧水 、 三正丁基氢锡 、 碳酸氢钠 、 溶剂黄146 、 硫脲 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 31.08h， 生成 methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  An access to various sulfation patterns in dermatan sulfate: chemical syntheses of sulfoforms of trisaccharide methyl glycosides

  摘要：

  The syntheses are reported for the first time of alpha-L-IdopA(2)SO(3)-(1-->3)-beta-D-GalpNAc4SO(3)-(1-->4)-alpha-L-IdopA2SO(3)-(1-->OMe), its disulfated analogue alpha-L-IdopA2SO(3)-(1-->3)-beta-D-GalpNAc4SO(3)-(1-->4)-alpha-L-IdopA2SO(3)-(1-->OMe), and of beta-D-GalpNAc4SO(3)-(1-->4)-alpha-L-IdopA2SO(3)-(1-->3)-beta-D-GalpNAc4SO(3)-(1-->OMe), which represent structural fragments of dermatan sulfate, unavailable directly by chemical or enzymatic degradation of the glycosaminoglycan polymer. These molecules were readily obtained from a pair of key disaccharide intermediates, in which the relative difference of stability of the D-GalNAc 4-hydroxy protecting groups (acetate or pivalate) toward saponification conditions allowed access to various sulfoforms from a common precursor. For the preparation of these blocks, the 4-O-pivaloyl-D-galacto moiety was readily obtained through a one-pot stereospecific intramolecular nucleophilic displacement on an easily available 3-O-pivaloyl-D-gluco precursor,and the L-IdoA moiety through selective radical oxidation at C-6 of a L-ido 4,6-diol derivative with oxoammonium salts. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00060-5