allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside | 701976-76-3

• 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-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: methyl (1R,5S,6R,8R,9S)-8-[(2R,3S,4R,5R,6S)-5-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-3-yl]oxy-3-(4-methoxyphenyl)-9-phenylmethoxy-2,4,7-trioxabicyclo[3.3.1]nonane-6-carboxylate
• CAS: 701976-76-3
• 化学式: C₄₅H₄₉N₃O₁₂
• 分子量: 823.897
• InChiKey: JJFGWEQDBBJHBS-UWOKZCDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  14

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-2-azido-3,6-di-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90%的产率得到allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranozide
  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：

  methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 camphor-10-sulfonic acid 、 potassium carbonate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 1.5h， 生成 allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-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

文献信息

• 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
  作者：Anna Dilhas、David Bonnaffé

  DOI：10.1016/j.tetlet.2004.03.046

  日期：2004.4

  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.