di(tert-butyl) (2S,4S)-4-[(tert-butyldimethylsilyl)oxy]-6-oxo-1,2-piperidinedicarboxylate | 653589-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: di(tert-butyl) (2S,4S)-4-[(tert-butyldimethylsilyl)oxy]-6-oxo-1,2-piperidinedicarboxylate
• CAS: 653589-32-3
• 化学式: C₂₁H₃₉NO₆Si
• 分子量: 429.629
• InChiKey: DSZMIXZFWMAAKV-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  di(tert-butyl) (2S,4S)-4-[(tert-butyldimethylsilyl)oxy]-6-oxo-1,2-piperidinedicarboxylate 在 LiEt₃BH₃ 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-piperidine-1,2-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

  摘要：

  tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-(OBu)-Bu-t and other beta-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy delta-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo-1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).

  DOI：

  10.1021/jo0353886
• 作为产物：
  描述：

  N-叔丁氧羰基-L-天冬氨酸 1-叔丁酯 在 咪唑 、 4-二甲氨基吡啶 、 sodium cyanoborohydride 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 80.0h， 生成 di(tert-butyl) (2S,4S)-4-[(tert-butyldimethylsilyl)oxy]-6-oxo-1,2-piperidinedicarboxylate
  参考文献：
  名称：

  Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

  摘要：

  tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-(OBu)-Bu-t and other beta-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy delta-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo-1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).

  DOI：

  10.1021/jo0353886

文献信息

• Synthesis of a Galactosylated 4-Hydroxylysine Building Block and Its Incorporation into a Collagen Immunodominant Glycopeptide
  作者：Julien Marin、Jean-Paul Briand、Gilles Guichard

  DOI：10.1002/ejoc.200700806

  日期：2008.2

  An analogue of the immunodominant glycopeptide from type II collagen encompassing residues 256–270 has been prepared by substituting β-D-galactopyranosyl-(2S,4R)-4-hydroxy-L-lysyl (Gal-4-Hyl) for β-D-galactopyranosyl-(2S,5R)-5-hydroxy-L-lysyl (Gal-5-Hyl) at position 264. The synthesis of the 4-hydroxylysine aglycon started from the known (2S,4S)-4-hydroxy-6-oxo-1,2-piperidinedicarboxylate (3) and involved

  通过用 β-D-吡喃半乳糖基-(2S,4R)-4-羟基-L-赖氨酰 (Gal-4-Hyl) 代替 β-D 制备了来自 II 型胶原蛋白的免疫显性糖肽类似物，包含残基 256-270 -吡喃半乳糖基-(2S,5R)-5-羟基-L-赖氨酰 (Gal-5-Hyl) 在 264 位。 4-羟基赖氨酸苷元的合成从已知的 (2S,4S)-4-羟基-6 开始-oxo-1,2-piperidinedicarboxylate (3) 并涉及 3 的选择性开环、内酯形成和内酯与甘氨酯的 N-酰化。得到的 N-Fmoc 保护的 4-羟基赖氨酰-甘氨酸二肽衍生物以高产率进行半乳糖基化，得到适合固相肽合成的结构单元。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)