azt analogues
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2022 ◽  
Vol 18 ◽  
pp. 95-101
Author(s):  
Sandeep Kumar ◽  
Jyotirmoy Maity ◽  
Banty Kumar ◽  
Sumit Kumar ◽  
Ashok K Prasad

Conformationally restricted diastereomeric homoarabinofuranosylpyrimidines (AZT analogue), i.e., (5′R)-3′-azido-3′-deoxy-2′-O,5′-C-bridged-β-ᴅ-homoarabinofuranosylthymine and -uracil had been synthesized starting from diacetone ᴅ-glucofuranose following chemoenzymatic and chemical routes in 34–35% and 24–25% overall yields, respectively. The quantitative and diastereoselective acetylation of primary hydroxy over two secondary hydroxy groups present in the key nucleoside precursor was mediated with Lipozyme® TL IM in 2-methyltetrahydrofuran following a chemoenzymatic pathway. Whereas, the protection of the primary hydroxy over the lone secondary hydroxy group in the key azido sugar precursor was achieved using bulky tert-butyldiphenylsilyl chloride (TBDPS-Cl) in pyridine in 92% yield following a chemical synthetic pathway. The chemoenzymatic method was found to be superior over the chemical method in respect of the number of synthetic steps and overall yield of the final product.


2010 ◽  
Vol 36 (4) ◽  
pp. 267-272 ◽  
Author(s):  
Mohammad Goodarzi ◽  
Matheus Puggina de Freitas

ChemInform ◽  
2007 ◽  
Vol 38 (46) ◽  
Author(s):  
Vincent Roy ◽  
Rachida Zerrouki ◽  
Pierre Krausz ◽  
Geraldine Laumond ◽  
Anne Marie Aubertin
Keyword(s):  

ChemInform ◽  
2007 ◽  
Vol 38 (36) ◽  
Author(s):  
Najim A. Al-Masoudi ◽  
Yaseen A. Al-Soud ◽  
Ibrahim A. I. Ali ◽  
Thilo Schuppler ◽  
Christoph Pannecouque ◽  
...  
Keyword(s):  

2007 ◽  
Vol 26 (5) ◽  
pp. 413-421 ◽  
Author(s):  
Vincent Roy ◽  
Rachida Zerrouki ◽  
Pierre Krausz ◽  
Géraldine Laumond ◽  
Anne Marie Aubertin
Keyword(s):  

2007 ◽  
Vol 26 (3) ◽  
pp. 223-230 ◽  
Author(s):  
Najim A. Al-Masoudi ◽  
Yaseen A. Al-Soud ◽  
Ibrahim A. I. Ali ◽  
Thilo Schuppler ◽  
Christoph Pannecouque ◽  
...  
Keyword(s):  

ChemInform ◽  
2006 ◽  
Vol 37 (33) ◽  
Author(s):  
El Sayed H. El Ashry ◽  
Adel Abdel-Rahman ◽  
Nagwa Rashed ◽  
Laila F. Awad ◽  
Hanaa A. Rasheed
Keyword(s):  

2006 ◽  
Vol 25 (3) ◽  
pp. 299-305 ◽  
Author(s):  
El Sayed H. El Ashry ◽  
Adel Abdel-Rahman ◽  
Nagwa Rashed ◽  
Laila F. Awad ◽  
Hanaa A. Rasheed
Keyword(s):  

ChemInform ◽  
2006 ◽  
Vol 37 (12) ◽  
Author(s):  
Evelyne Migianu ◽  
Maelle Monteil ◽  
Pascale Even ◽  
Marc Lecouvey
Keyword(s):  

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