(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetamidoyl-α-D-galactopyranoside | 445397-68-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetamidoyl-α-D-galactopyranoside
• 英文别名: methyl (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetyloxy-2-(phenylmethoxymethyl)-5-[(2,2,2-trichloroacetyl)amino]-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxy-5-benzoyloxy-3-(2-chloroacetyl)oxy-4-phenylmethoxyoxane-2-carboxylate
• CAS: 445397-68-2
• 化学式: C₄₂H₄₁Cl₇N₂O₁₅
• 分子量: 1061.96
• InChiKey: ALZYLAIMXBFNHG-JITWCFDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  66
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  214
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetamidoyl-α-D-galactopyranoside 在 lithium hydroxide 、 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 、 硫脲 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 20.0h， 生成 methyl O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-4-O-acetyl-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
• 作为产物：
  描述：

  4-methoxyphenyl 3-O-benzyl-α-L-idopyranoside 在 potassium bromide 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 calcium hypochlorite 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 9.08h， 生成 (methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetamidoyl-α-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

文献信息

• An access to various sulfation patterns in dermatan sulfate: chemical syntheses of sulfoforms of trisaccharide methyl glycosides
  作者：Nadine Barroca、Jean-Claude Jacquinet

  DOI：10.1016/s0008-6215(02)00060-5

  日期：2002.4

  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.