1-tert-butyl (2S,5R)-6-azido-2-[N-(tert-butoxycarbonyl)-amino]-5-hydroxyhexanoate | 220244-00-8

• 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: 1-tert-butyl (2S,5R)-6-azido-2-[N-(tert-butoxycarbonyl)-amino]-5-hydroxyhexanoate
• 英文别名: tert-butyl (2S,5R)-6-azido-5-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 220244-00-8
• 化学式: C₁₅H₂₈N₄O₅
• 分子量: 344.411
• InChiKey: LAVFXTISZHDGCQ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-tert-butyl (2S,5R)-6-azido-2-[N-(tert-butoxycarbonyl)-amino]-5-hydroxyhexanoate 在 10percent Pd/C 盐酸 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 生成 (2S,5R)-(+)-hydroxylysine dihydrochloride
  参考文献：
  名称：

  Diastereoselective Hydroxylation of 6-Substituted Piperidin-2-ones. An Efficient Synthesis of (2S,5R)-5-Hydroxylysine and Related α-Amino Acids

  摘要：

  The synthesis of (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylates (5) and related (3S,W-3hydroxy-6-alkyl-2-oxo-1-piperidinecarboxylates has been developed. The approach is based on the asymmetric hydroxylation of enolates generated from the corresponding N-protected-6-substituted piperidin-2-ones. The utility of 5a as a precursor in the synthesis of (2S,5R)-5-hydroxylysine (1), an amino acid unique to collagen and collagen-like proteins, has also been demonstrated. (2S)-6oxo-1,2-piperidinedicarboxylates (6) required for hydroxylation studies were prepared in 38-74% yield, starting from conveniently protected aspartic acid as inexpensive chiral adduct. Hydroxylation of 6 to 5 proceeds in high yield and excellent diastereoselectivity by treatment of their Li-enolate with (+)-camphorsulfonyloxaziridine at -78 degreesC. Ring opening of di-tert-butyl (2S,5R)-6-oxo-1,2-piperidinedicarboxylate ((5R)-5a) under reductive conditions afforded the corresponding 1,2-diol (17) in 91%, which was further transformed to (2S,5R)-5-hydroxylysine in four steps (84%). 17 is also a versatile intermediate in the preparation of tert-butyl (2S,M)-2-[(tert-butoxycarbonyl)aminol 5-hydroxy-6-iodohexanoate (3) and tert-butyl (2S)-2-[(tert-butoxycarbonyl)aminol-4-[(2,R)-oxiranyl]- butanoate (4), two amino acid derivatives used in the total synthesis of the bone collagen cross-link (+)-pyridinoline (2a).

  DOI：

  10.1021/jo025950c
• 作为产物：
  描述：

  Boc-L-谷氨酸-1-叔丁酯 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium tetrahydroborate 、 sodium azide 、 氢溴酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.84h， 生成 1-tert-butyl (2S,5R)-6-azido-2-[N-(tert-butoxycarbonyl)-amino]-5-hydroxyhexanoate
  参考文献：
  名称：

  Collagen cross-links: Synthesis of pyridinoline, deoxypyridinoline and their analogues

  摘要：

  DOI：

  10.1016/s0040-4020(98)01023-0

文献信息

• N-Glycosylated type II collagen peptides as therapeutic saccharide vaccines for rheumatoid arthritis
  作者：Dake Liu、Shuyan Liu、Fanlei Hu、Zhongtang Li、Zhongjun Li

  DOI：10.1016/j.cclet.2023.108762

  日期：2024.5

  interaction among type II collagen (CII), human DR4 major histocompatibility complex type II molecule (MHC II) and T-cell receptor (TCR) is associated with the development of rheumatoid arthritis (RA). The activation of T cells can be reduced through exposure to modified CII(263–272) glycopeptide fragment competitive inhibition with self-antigen. In this work, 30 peptides based on the sequence of CII(263–272)

  II 型胶原 (CII)、人类 DR4 主要组织相容性复合体 II 型分子 (MHC II) 和 T 细胞受体 (TCR) 之间的相互作用与类风湿性关节炎 (RA) 的发生有关。通过暴露于修饰的 CII(263–272) 糖肽片段与自身抗原的竞争性抑制，可以减少 T 细胞的活化。在这项工作中，制备了 30 种基于 CII(263-272) 序列的肽，并通过表面等离子共振 (SPR) 测定评估了它们与 DR4 蛋白的结合。还研究了胶原诱导的类风湿性关节炎（CIA）小鼠脾细胞对促炎因子分泌的影响。两个-糖基化的CII肽被鉴定为与人重组DR4蛋白具有强结合力并且具有弱的促炎作用。这些糖肽可以开发为治疗类风湿性关节炎（RA）的治疗性糖疫苗。
• Synthesis of an Azido Precursor to (2<i>S</i>,5<i>R</i>)-5-Hydroxylysine Using an Asymmetric Organocatalytic Chlorination/Reduction Sequence
  作者：Manuel Johannes、Margaret A. Brimble

  DOI：10.1021/jo402220s

  日期：2013.12.20

  An efficient, robust, and scalable synthesis of an azido precursor to the modified amino acid (2S,5R)-5-hydroxylysine was developed on the basis of the use of a highly stereoselective organocatalytic alpha-chlorination-reduction protocol. The final Fmoc-protected (2S,5R)-6-azido-5-hydroxylysine derivative can be used in solid-phase peptide synthesis, providing access to proteins that contain large quantities of post-translationally modified lysine (e.g., collagens).