51820-70-3Relevant academic research and scientific papers
Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine
Liu, Tongchao,Tang, Jiadeng,Liang, Jianpeng,Chen, Yabin,Wang, Xiaowen,Shen, Jingkang,Zhao, Dongmei,Xiong, Bing,Cen, Jun-Da,Chen, Yue-Lei
, p. 1203 - 1213 (2019)
Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.
Synthesis of photolabile o-nitroveratryloxycarbonyl (NVOC) protected peptide nucleic acid monomers
Liu, Zheng-Chun,Shin, Dong-Sik,Lee, Kyu-Teak,Jun, Bong-Hyun,Kim, Yong-Kweon,Lee, Yoon-Sik
, p. 7967 - 7973 (2007/10/03)
The chemical synthesis of peptide nucleic acid (PNA) monomers was accomplished using various combinations of the o-nitroveratryloxycarbonyl (NVOC) group (N-aminoethylglycine backbone) and base labile acyl-type nucleobase protecting groups (anisoyl for ade
A direct synthesis of nucleoside analogs homologated at the 3′- and 5′-positions
Schmidt, Juergen,Eschgfaeller, Bernd,Benner, Steven A.
, p. 2937 - 2958 (2007/10/03)
A new route is presented to prepare analogs of nucleosides homologated at the 3′- and 5′-positions. This route, applicable to both the D- and L-enantiomeric forms, is suitable for the preparation of monomeric bis-homonucleosides needed for the synthesis o
Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers
Timar, Zoltan,Kovacs, Lajos,Kovacs, Gyoergyi,Schmel, Zoltan
, p. 19 - 26 (2007/10/03)
The chemical synthesis of polyamide (peptide) nucleic acid (PNA) monomers 22-25 has been accomplished using Fmoc [N-(2-aminoethyl)glycine backbone], anisoyl (adenine), 4-tert-butylbenzoyl (cytosine) and isobutyryl/ diphenylcarbamoyl (guanine) protecting-group combinations, thus allowing oligomer synthesis on both peptide and oligonucleotide synthesizers. An alternative method for the preparation of (N6-anisoyladenin-9-yl)acetic acid 7 is described using partial hydrolysis of a dianisoylated derivative. Different methods were studied for guanine alkylation including (a) Mitsunobu reaction; (b) low-temperature, sodium hydride- and (c) N, N-diisopropylethylaminemediated alkylation reactions to give preferentially N9-substituted derivatives. Empirical rules are proposed for differentiating N9/N7-substituted guanines based on their 13C NMR chemical-shift differences. The Royal Society of Chemistry 2000.
