(2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 870001-87-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 870001-87-9
• 化学式: C₃₅H₅₃N₃O₁₆Si
• 分子量: 799.902
• InChiKey: WLPQLSUIGJACQF-RGPIFJMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  55.0
• 可旋转键数：
  21.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  238.8
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 三甲基氨基磺酸 作用下， 反应 20.0h， 生成 (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-6-sulfooxymethyl-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Orthogonal Sulfation Strategy for Synthetic Heparan Sulfate Ligands

  摘要：

  An orthogonal sulfation strategy involving six different protecting groups has been developed for generating sulfated carbohydrate libraries based on heparan. Chemoselective cleavage conditions (optimized for a heparan disaccharide) can be performed in the presence of sulfate esters as well as the remaining protecting groups.

  DOI：

  10.1021/ol052130o
• 作为产物：
  描述：

  Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester 在 2,6-二叔丁基-4-甲基吡啶 咪唑 、 4-二甲氨基吡啶 、 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 4 A molecular sieve 、 triflic azide 、 四丁基氟化铵 、 sodium methylate 、 potassium carbonate 、 氟化氢吡啶 、 copper(II) sulfate 、 乙二胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 113.0h， 生成 (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Orthogonal Sulfation Strategy for Synthetic Heparan Sulfate Ligands

  摘要：

  An orthogonal sulfation strategy involving six different protecting groups has been developed for generating sulfated carbohydrate libraries based on heparan. Chemoselective cleavage conditions (optimized for a heparan disaccharide) can be performed in the presence of sulfate esters as well as the remaining protecting groups.

  DOI：

  10.1021/ol052130o