1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose | 175978-71-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose
• 英文别名: [(2S,3R,4S,5R,6R)-3,5,6-tribenzoyloxy-4-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 175978-71-9
• 化学式: C₄₁H₃₄O₁₀
• 分子量: 686.715
• InChiKey: GALCYWIRRKZYFE-RMNOJEGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose 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 、 sodium methylate 、 碳酸氢钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 10.58h， 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
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 、 苯甲酰氯 在 硫酸 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 为溶剂， 反应 10.0h， 以62%的产率得到1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose
  参考文献：
  名称：

  硫酸皮肤素二糖片段β-d-GalpNAc4SO3-（1→4）-1-IdopA2SO3及其甲基α-1-糖苷衍生物的合成

  摘要：

  摘要二糖（2-乙酰氨基-2-脱氧-4-O-磺基磺酸钠-β-d-吡喃并吡喃糖基）-（1→4）-（2-O-磺基磺酸钠-异吡喃钠）二糖酸钠的合成首次报道了硫酸皮肤素的片段及其甲基α-1-糖苷衍生物。由ad-葡萄糖前体容易制备的4-O-乙酰基-3,6-二-O-苄基-2-脱氧-2-三氯乙酰胺基-1-O-三氯乙酰亚胺基-α-d-吡喃半乳糖的使用使立体控制和与1-异戊二酸酯衍生物的低反应性4-羟基偶合的高产率偶联。高收率地实现了二糖产物向目标分子的经典转化。

  DOI：

  10.1016/s0008-6215(00)00234-2

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.
• Syntheses of β-d-GalpNAc4SO3-(1→4)-l-IdopA2SO3, a disaccharide fragment of dermatan sulfate, and of its methyl α-l-glycoside derivative
  作者：Nadine Barroca、Jean-Claude Jacquinet

  DOI：10.1016/s0008-6215(00)00234-2

  日期：2000.11

  Abstract The syntheses of sodium (sodium 2-acetamido-2-deoxy-4-O-sulfonato-β- d -galactopyranosyl)-(1→4)-(sodium 2-O-sulfonato- l -idopyran)uronate, a disaccharide fragment of dermatan sulfate, and of its methyl α- l -glycoside derivative are reported for the first time. The use of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α- d -galactopyranose, readily prepared

  摘要二糖（2-乙酰氨基-2-脱氧-4-O-磺基磺酸钠-β-d-吡喃并吡喃糖基）-（1→4）-（2-O-磺基磺酸钠-异吡喃钠）二糖酸钠的合成首次报道了硫酸皮肤素的片段及其甲基α-1-糖苷衍生物。由ad-葡萄糖前体容易制备的4-O-乙酰基-3,6-二-O-苄基-2-脱氧-2-三氯乙酰胺基-1-O-三氯乙酰亚胺基-α-d-吡喃半乳糖的使用使立体控制和与1-异戊二酸酯衍生物的低反应性4-羟基偶合的高产率偶联。高收率地实现了二糖产物向目标分子的经典转化。