(2R,3R,4R,5S)-4-benzoyloxy-3-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine | 927809-76-5

• 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-benzoyloxy-3-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine
• 英文别名: [(2S,3R,4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(hydroxymethyl)-4-phenylmethoxypyrrolidin-3-yl] benzoate
• CAS: 927809-76-5
• 化学式: C₃₆H₄₁NO₅Si
• 分子量: 595.811
• InChiKey: UEZGRYTXOHBXAE-KRFMAMIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-4-benzoyloxy-3-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 、 苯甲酰氯 、 氯甲酸苄酯 在 TEA 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以3.5 g的产率得到(2S,3R,4R,5R)-2'-O-benzoyl-3-benzoyloxy-4-benzyloxy-N-benzyloxycarbonyl-5'-O-tertbutyldiphenylsilyl-2,5-bis(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
• 作为产物：
  描述：

  10-(benzyloxy)-2,2-dimethyl-1,3,6-trioxaspiro(4,5)decane-8,9-diol 在 镍 吡啶 、 咪唑 、 偶氮二甲酸二异丙酯 、 二苯基磷酸 、 氢气 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 26.5h， 生成 (2R,3R,4R,5S)-4-benzoyloxy-3-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(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