191655-63-7

Upstream product

• 191655-44-4 (2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester 
• 191655-45-5 (2S)‐2‐{[(tert‐butoxy)carbonyl]amino}‐4‐[(tert‐butyldimethylsilyl)oxy]butanoic acid 
• 191655-46-6 tert-butyl (S)-(4-((tert-butyldimethylsilyl)oxy)-1-hydroxybutan-2-yl)carbamate 
• 105183-60-6 (S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate 
• 220418-64-4 [2-tert-butoxycarbonylamino-4-(tetrahydro-pyran-2-yloxy)-butoxy]-acetic acid tert-butyl ester 
• 220418-62-2 2-tert-butoxycarbonylamino-4-(tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester 
• 220418-63-3 [1-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester 
• 147325-09-5 N-Boc-L-homoserine ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 4330-20-5 N-3-benzoylthymine 
• 220418-65-5 tert-butyl 7-hydroxy-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate 

Relevant academic research and scientific papers

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

Syntheses of 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).

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

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 drains by way of a Mitsunobu reaction. Cytosine derivatives were prepared through uracil → cytosine base conversion at the stage of N(δ)-BOC protected amino acid tert-butyl esters.