Phosphoric acid dibenzyl ester (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester | 208656-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phosphoric acid dibenzyl ester (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester
• CAS: 208656-40-0
• 化学式: C₄₁H₄₃O₉P
• 分子量: 710.761
• InChiKey: GISTZCCMFOBSQW-LRHJBHCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.02
• 重原子数：
  51.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 Phosphoric acid dibenzyl ester (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到Benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  An Expeditious Route toStreptococciandEnterococciGlycolipidsViaRing-Opening of 1,2-Anhydrosugars with Protic Acids

  摘要：

  1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly beta-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the beta-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective alpha-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected alpha-diglucosyl glycerol derivative 25, which upon desilylation (-->28), acylation (-->29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.

  DOI：

  10.1080/07328309808002906
• 作为产物：
  描述：

  磷酸二苄酯 、 3,4,6-tri-O-benzyl-D-glucal epoxide 以 二氯甲烷 为溶剂， 反应 0.08h， 以82%的产率得到Phosphoric acid dibenzyl ester (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  An Expeditious Route toStreptococciandEnterococciGlycolipidsViaRing-Opening of 1,2-Anhydrosugars with Protic Acids

  摘要：

  1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly beta-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the beta-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective alpha-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected alpha-diglucosyl glycerol derivative 25, which upon desilylation (-->28), acylation (-->29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.

  DOI：

  10.1080/07328309808002906