methyl 2-azido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside | 625824-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-azido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside
• 英文别名: (2S,4aR,6S,7R,8R,8aR)-7-azido-6-methoxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 625824-98-8
• 化学式: C₁₅H₁₉N₃O₆
• 分子量: 337.332
• InChiKey: RBEYVQPAZVAAFN-JNWWKETESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside 在 4-二甲氨基吡啶 、 4 A molecular sieve 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 methyl 2-azido-3-O-benzoyl-2-deoxy-6-O-(4-methoxybenzyl)-4-O-trifluoromethanesulfonate-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a S-linked heparan sulfate trisaccharide as the substrate mimic of heparanase

  摘要：

  An approach to the Construction of the beta-(1 -> 4)-S-linkage between a glucuronic and a glucosamine unit, and then to the synthesis of a heparan sulfate trisaccharide containing such a linkage (1) as a nonhydrolyzable substrate mimic of heparanase was developed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.088
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 、 methyl 2-azido-2-deoxy-D-galactopyranoside 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以33%的产率得到methyl 2-azido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a S-linked heparan sulfate trisaccharide as the substrate mimic of heparanase

  摘要：

  An approach to the Construction of the beta-(1 -> 4)-S-linkage between a glucuronic and a glucosamine unit, and then to the synthesis of a heparan sulfate trisaccharide containing such a linkage (1) as a nonhydrolyzable substrate mimic of heparanase was developed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.088

文献信息

• Synthesis of a S-linked heparan sulfate trisaccharide as the substrate mimic of heparanase
  作者：Hongzhi Cao、Biao Yu

  DOI：10.1016/j.tetlet.2005.04.088

  日期：2005.6

  An approach to the Construction of the beta-(1 -> 4)-S-linkage between a glucuronic and a glucosamine unit, and then to the synthesis of a heparan sulfate trisaccharide containing such a linkage (1) as a nonhydrolyzable substrate mimic of heparanase was developed. (c) 2005 Elsevier Ltd. All rights reserved.