(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-6-allyloxy-5-azido-4-benzyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-3,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 701976-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-6-allyloxy-5-azido-4-benzyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-3,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 701976-75-2
• 化学式: C₃₂H₃₉N₃O₁₂
• 分子量: 657.675
• InChiKey: FKNPHAHPYXKPNT-XYKWZPDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  197.2
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-6-allyloxy-5-azido-4-benzyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-3,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 三乙基硅烷 、 4 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 allyl [methyl 2-O-acetyl-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：

  methyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranyluronate trichloroacetimidate 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-6-allyloxy-5-azido-4-benzyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-3,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  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