tert-butyl 7-hydroxy-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate | 220418-65-5

• 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: tert-butyl 7-hydroxy-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate
• 英文别名: tert-butyl 2-[(2S)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butoxy]acetate
• CAS: 220418-65-5
• 化学式: C₁₅H₂₉NO₆
• 分子量: 319.398
• InChiKey: VDKJJMVUOHOZSK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 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：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 7-hydroxy-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  Polyamide based nucleic acid analogs — synthesis of δ-amino acids with nucleic acid bases bearing side chains

  摘要：

  Nucleoamino acids of type I - III have been synthesized, which can serve as building blocks for novel polyamide based nucleic acid analogs. Key steps in the syntheses are the alkylation of serinol I and homoserinol 18 with tert-butyl bromoacetate or tert-butyl bromopropionate under phase transfer conditions and the introduction of thymine or uracil into the amino acid side chains by way of a Mitsunobu reaction. Cytosine derivatives were prepared through uracil --> cytosine base conversion at the stage of N-delta-BOC protected amino acid tert-butyl esters. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00172-8
• 作为产物：
  描述：

  [(S)-2-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butoxy]-acetic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以89%的产率得到tert-butyl 7-hydroxy-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate
  参考文献：
  名称：

  Polyamide based nucleic acid analogs — synthesis of δ-amino acids with nucleic acid bases bearing side chains

  摘要：

  Nucleoamino acids of type I - III have been synthesized, which can serve as building blocks for novel polyamide based nucleic acid analogs. Key steps in the syntheses are the alkylation of serinol I and homoserinol 18 with tert-butyl bromoacetate or tert-butyl bromopropionate under phase transfer conditions and the introduction of thymine or uracil into the amino acid side chains by way of a Mitsunobu reaction. Cytosine derivatives were prepared through uracil --> cytosine base conversion at the stage of N-delta-BOC protected amino acid tert-butyl esters. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00172-8

文献信息

• Synthesis of δ-amino acids with an ether linkage in the main chain and nucleobases on the side chain as monomer units for oxy-peptide nucleic acids
  作者：Masayasu Kuwahara、Miki Arimitsu、Masahiko Sisido

  DOI：10.1016/s0040-4020(99)00541-4

  日期：1999.8

  four N-Fmoc δ-amino acids with an ether linkage in the main chain and four different nucleobases on the side chain, Fmoc-NH-C∗H(CH2-CH2-B)-CH2-O-CH2-COOH (B =thymine, uracil, N4-benzoylcytosine, and N2-isobutyrylguanine) are described. The δ-amino acids were prepared through 8–12 step synthesis starting from l-homoserine and could be linked together to form novel peptide nucleic acids (oxy-PNAs = OPNAs)

  Fmoc-NH-C * H（CH 2 -CH 2 -B）-CH 2 -O-CH合成四个在主链上带有醚键且在侧链上具有四个不同核碱基的N -Fmocδ-氨基酸描述了2- COOH（B ＝胸腺嘧啶，尿嘧啶，N 4-苯甲酰基胞嘧啶和N 2-异丁酰基鸟嘌呤）。δ-氨基酸是通过从1-高丝氨酸开始的8–12步合成制备的，可以连接在一起形成新的肽核酸（氧基-PNAs = OPNAs）。