5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-β-D-fructopyranose | 927809-67-4

• 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: 5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-β-D-fructopyranose
• 英文别名: [(2R,3S,4R,5R)-5-azido-2-hydroxy-2-(hydroxymethyl)-3-phenylmethoxyoxan-4-yl] benzoate
• CAS: 927809-67-4
• 化学式: C₂₀H₂₁N₃O₆
• 分子量: 399.403
• InChiKey: FQJXANIWWPSZBG-FTEYMNFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-β-D-fructopyranose 在 咪唑 、 镍 四丁基氟化铵 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0 ℃ 、482.63 kPa 条件下， 反应 103.0h， 生成 2,5-二(羟基甲基)-3,4-吡咯烷二醇
  参考文献：
  名称：

  Polyhydroxylated pyrrolidines: synthesis from d-fructose of new tri-orthogonally protected 2,5-dideoxy-2,5-iminohexitols

  摘要：

  The readily available 3-O-benzyl-1,2-O-isopropylidene-beta-D-fructopyranosc (2) was transformed into its 5-O-(3) and 4-O-benzoyl (4) derivative. Compound 4 was straightforwardly transformed into 5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-beta D-fructopyranose (7) via the corresponding 5-deoxy-5-iodo-alpha-L-sorbopyranose derivative 6. Cleavage of the acetonide in 7 to give 8, followed by regioselective 1-O-silylation to 9 and subsequent catalytic hydrogenation gave a mixture of (2S,3R,4R,5R)-(10) and (2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (12) that was resolved after chemoselective N-protection as their Cbz derivatives 11 and la, respectively. Stereochemistry of 11 and la could be determined after total deprotection of 11 to the well known DGDP (13). Compound 2 was similarly transformed into the tri-orthogonally protected DGDP derivative 18. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.070
• 作为产物：
  描述：

  4-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose 在 咪唑 、 叠氮化锂 、 碘 、 三苯基膦 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-β-D-fructopyranose
  参考文献：
  名称：

  Polyhydroxylated pyrrolidines: synthesis from d-fructose of new tri-orthogonally protected 2,5-dideoxy-2,5-iminohexitols

  摘要：

  The readily available 3-O-benzyl-1,2-O-isopropylidene-beta-D-fructopyranosc (2) was transformed into its 5-O-(3) and 4-O-benzoyl (4) derivative. Compound 4 was straightforwardly transformed into 5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-beta D-fructopyranose (7) via the corresponding 5-deoxy-5-iodo-alpha-L-sorbopyranose derivative 6. Cleavage of the acetonide in 7 to give 8, followed by regioselective 1-O-silylation to 9 and subsequent catalytic hydrogenation gave a mixture of (2S,3R,4R,5R)-(10) and (2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (12) that was resolved after chemoselective N-protection as their Cbz derivatives 11 and la, respectively. Stereochemistry of 11 and la could be determined after total deprotection of 11 to the well known DGDP (13). Compound 2 was similarly transformed into the tri-orthogonally protected DGDP derivative 18. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.070

文献信息

• Polyhydroxylated pyrrolidines: synthesis from d-fructose of new tri-orthogonally protected 2,5-dideoxy-2,5-iminohexitols
  作者：Isidoro Izquierdo、María T. Plaza、Victor Yáñez

  DOI：10.1016/j.tet.2006.11.070

  日期：2007.2

  The readily available 3-O-benzyl-1,2-O-isopropylidene-beta-D-fructopyranosc (2) was transformed into its 5-O-(3) and 4-O-benzoyl (4) derivative. Compound 4 was straightforwardly transformed into 5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-beta D-fructopyranose (7) via the corresponding 5-deoxy-5-iodo-alpha-L-sorbopyranose derivative 6. Cleavage of the acetonide in 7 to give 8, followed by regioselective 1-O-silylation to 9 and subsequent catalytic hydrogenation gave a mixture of (2S,3R,4R,5R)-(10) and (2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (12) that was resolved after chemoselective N-protection as their Cbz derivatives 11 and la, respectively. Stereochemistry of 11 and la could be determined after total deprotection of 11 to the well known DGDP (13). Compound 2 was similarly transformed into the tri-orthogonally protected DGDP derivative 18. (c) 2006 Elsevier Ltd. All rights reserved.