(2R,3R,4R,5S)-4,5-Dihydroxy-3-((3aS,4R,6R,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester | 184830-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R,5S)-4,5-Dihydroxy-3-((3aS,4R,6R,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (2R,3R,4R,5S)-3-[[(3aS,4R,6R,7R,7aR)-7-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)piperidine-1-carboxylate
• CAS: 184830-05-5
• 化学式: C₂₃H₃₃NO₁₁
• 分子量: 499.515
• InChiKey: ARWUZAOYRXALSB-ODKIBMNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  168
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-4,5-Dihydroxy-3-((3aS,4R,6R,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  An Efficient Synthesis of Sulfo Lewis X Analog Containing 1-Deoxynojirimycin

  摘要：

  Sulfo Lewis(x) analog containing 1-deoxynojirimycin (13) has been efficiently synthesized. Glycosidation of ethyl 2,3,4-tri-0-benzyl-1-thio-beta-D-fucopyranoside (5) with O-(2,6-di-O-benzoyl-3,4-isopropylidene-beta-D-galactopyranosyl)-(1-->4)-2, 6-di-O-benzoyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (4), prepared from O-beta-D-galactopyranosyl-(1-->4)-1,5-dideoxy-1, 5-imino-D-glucitol (1) via 3 steps, and subsequent acid hydrolysis of the isopropylidene group gave the desired trisaccharide diol derivative (7) in good yield. Compound 7 was easily converted into 3'-O-sulfo Lewis(x) analog (13) via 6 steps in high yield.

  DOI：

  10.1080/07328309808002348
• 作为产物：
  描述：

  4-O-β-D-galactopyranosyl-(1->4)-1,5-dideoxy-1,5-imino-D-glucitol 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2R,3R,4R,5S)-4,5-Dihydroxy-3-((3aS,4R,6R,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  An Efficient Synthesis of Sulfo Lewis X Analog Containing 1-Deoxynojirimycin

  摘要：

  Sulfo Lewis(x) analog containing 1-deoxynojirimycin (13) has been efficiently synthesized. Glycosidation of ethyl 2,3,4-tri-0-benzyl-1-thio-beta-D-fucopyranoside (5) with O-(2,6-di-O-benzoyl-3,4-isopropylidene-beta-D-galactopyranosyl)-(1-->4)-2, 6-di-O-benzoyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (4), prepared from O-beta-D-galactopyranosyl-(1-->4)-1,5-dideoxy-1, 5-imino-D-glucitol (1) via 3 steps, and subsequent acid hydrolysis of the isopropylidene group gave the desired trisaccharide diol derivative (7) in good yield. Compound 7 was easily converted into 3'-O-sulfo Lewis(x) analog (13) via 6 steps in high yield.

  DOI：

  10.1080/07328309808002348