allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside | 701976-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS: 701976-78-5
• 化学式: C₄₀H₄₅N₃O₁₃
• 分子量: 775.81
• InChiKey: QEYSHLFKBFXXGU-IJJYIGOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  56.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  184.43
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 在 三乙基硅烷 、 4 A molecular sieve 、 二氯苯酚溴酯 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以84%的产率得到allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  PhBCl2 promoted reductive opening of 2′,4′-O-p-methoxybenzylidene: new regioselective differentiation of position 2′ and 4′ of α-l-iduronyl moieties in disaccharide building blocks

  摘要：

  We describe a new protocol for the challenging differentiation of the position 2' and 4' of L-iduronyl moieties located at the nonreducing end of various disaccharide building blocks. This methodology is based on the introduction of a 2',4'-O-p-methoxybenzylidene group, followed by a totally regioselective reductive opening of this acetal by the PhBCl2/Et3SiH reagent system, L-Iduronyl moieties protected by a 4'-O-p-methoxybenzyl group were thus obtained regioselectively and efficiently. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.046
• 作为产物：
  描述：

  allyl (methyl 3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 在 偶氮二甲酸二异丙酯 、 camphor-10-sulfonic acid 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  PhBCl2 promoted reductive opening of 2′,4′-O-p-methoxybenzylidene: new regioselective differentiation of position 2′ and 4′ of α-l-iduronyl moieties in disaccharide building blocks

  摘要：

  We describe a new protocol for the challenging differentiation of the position 2' and 4' of L-iduronyl moieties located at the nonreducing end of various disaccharide building blocks. This methodology is based on the introduction of a 2',4'-O-p-methoxybenzylidene group, followed by a totally regioselective reductive opening of this acetal by the PhBCl2/Et3SiH reagent system, L-Iduronyl moieties protected by a 4'-O-p-methoxybenzyl group were thus obtained regioselectively and efficiently. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.046