(2S,3R,4R,5R)-4-(benzoyloxy)-3-(benzyloxy)-1-(benzyloxycarbonyl)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(hydroxymethyl)pyrrolidine | 927809-70-9

• 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: (2S,3R,4R,5R)-4-(benzoyloxy)-3-(benzyloxy)-1-(benzyloxycarbonyl)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(hydroxymethyl)pyrrolidine
• 英文别名: (2S,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine；benzyl (2S,3R,4R,5R)-4-benzoyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(hydroxymethyl)-3-phenylmethoxypyrrolidine-1-carboxylate
• CAS: 927809-70-9
• 化学式: C₄₄H₄₇NO₇Si
• 分子量: 729.945
• InChiKey: WEKQUUWMZMTJRH-LLIMXKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-4-(benzoyloxy)-3-(benzyloxy)-1-(benzyloxycarbonyl)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(hydroxymethyl)pyrrolidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到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：

  5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-β-D-fructopyranose 在 咪唑 、 镍 氢气 、 potassium carbonate 作用下， 以 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 96.0h， 生成 (2S,3R,4R,5R)-4-(benzoyloxy)-3-(benzyloxy)-1-(benzyloxycarbonyl)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(hydroxymethyl)pyrrolidine
  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 of Trideoxy-2,5-iminohexitols
  作者：Isidoro Izquierdo、María Plaza、Juan Tamayo、Daniele Lo Re、Fernando Sánchez-Cantalejo

  DOI：10.1055/s-2008-1072566

  日期：2008.5

  A series of naturally occurring pyrrolidine alkaloids and analogues, with the general structure of trideoxy-2,5-iminohexitols (imino- or azasugars), have been enantiosynthesized using triorthogonally protected pyrrolidines, previously prepared from commercial d-fructose, as homochiral starting materials. The inhibitory activity of some of the described compounds against glycosidases and glycosyltransferases makes them potential therapeutic agents.

  利用以前从商用 d-果糖中制备的三正对映体保护的吡咯烷作为同手性起始原料，合成了一系列天然存在的吡咯烷生物碱和类似物，其一般结构为三脱氧-2,5-亚氨基己糖醇（亚氨基或氮杂杉糖）。其中一些化合物对糖苷酶和糖基转移酶具有抑制活性，因此具有潜在的治疗作用。