(2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-piperidine-1-carboxylic acid benzyl ester | 162872-40-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-piperidine-1-carboxylic acid benzyl ester
• CAS: 162872-40-4
• 化学式: C₂₀H₂₉NO₁₁
• 分子量: 459.45
• InChiKey: GHZAZXDLOHNCEM-ZOLPUKQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.09
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  189.61
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-piperidine-1-carboxylic acid benzyl ester 在 对甲苯磺酸 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 benzyl (2R,3R,4R,5S)-3-[[(3aS,4R,6R,7R,7aS)-7-benzoyloxy-4-(benzoyloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-5-benzoyloxy-2-(benzoyloxymethyl)-4-hydroxypiperidine-1-carboxylate
  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 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 氯仿 、 水 为溶剂， 生成 (2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-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