Benzoyl Cyanide: A Mild and Efficient Reagent for Benzoylation of Nucleosides

References

• Schaller , H. , Weimann , G. , Lerch , B. and Khorana , H. G. 1963 . The stepwise synthesis of specific deoxyribopolynucleotides: protected derivatives of deoxyribonucleosides and new synthesis of deoxyribonucleosides‐3′ phosphates . J. Am. Chem. Soc. , 85 : 3821 – 3827 .
   Web of Science ®Google Scholar
• Zhu , X.‐F. , Williams , H. J. Jr. and Scott , A. I. 2003 . An improved transient method for the synthesis of N‐benzoylated nucleosides . Synth. Commun. , 33 : 1233 – 1243 .
   Web of Science ®Google Scholar
• Rao , N. S. , Kumar , P. , Chauhan , V. K. , Garg , B. S. and Gupta , K. C. 2002 . Microwave assisted high yielding preparation of N‐protected 2′‐deoxyribonucleosides useful for oligonucleotide synthesis . Nucleosides, Nucleotides & Nucleic Acids , 21 : 393 – 400 .
   PubMed Web of Science ®Google Scholar
• Uzagare , M. C. , Sanghvi , Y. S. and Salunkhe , M. M. 2003 . Application of ionic liquid 1‐methoxyethyl‐3‐methyl imidazolium methanesulphonate in nucleoside chemistry . Green Chemistry , : 370 – 372 .
   Google Scholar
• Prasad , A. K. and Wengel , J. 1996 . Enzyme‐mediated protecting group chemistry on the hydroxyl groups of nucleosides . Nucleosides Nucleotides , 15 : 1347 – 1359 .
   Google Scholar
• Stawinski , J. , Hozumi , T. and Narang , S. A. 1976 . Benzoyltetrazole: A mild benzoylating reagent for nucleosides . J. Chem. Soc., Chem. Commun. , : 243 – 244 .
   Google Scholar
• Abbas , S. A. and Haines , A. H. 1975 . Benzoyl cyanide as a selective acylating agent . Carbohydr. Res. , 39 : 358 – 363 .
   Web of Science ®Google Scholar
• Murahashi , S.‐T. and Naota , T. 1993 . Ruthenium‐catalyzed oxidations for selective synthesis of ketones and acyl cyanides: selective acylation of amino compounds with acyl cyanides . Synthesis , : 433 – 440 .
   Google Scholar
• Holy , A. and Soucek , M. 1971 . Benzoyl cyanide—a new benzoylating agent in nucleoside and nucleotide chemistry . Tetrahedron Lett. , : 185 – 188 .
   PubMed Web of Science ®Google Scholar
• Havel , M. , Velek , J. , Prospisek , J. and Soucek , M. 1979 . Selective acylation of hydroxy steroids with acyl cyanides . Collect. Czech. Chem. Commun. , 44 : 2443 – 2446 .
   Google Scholar
• Soll , R. M. and Seitz , S. P. 1987 . Synthetic studies on boron containing antibiotics . Tetrahedron Lett. , 28 : 5457 – 5460 .
   Google Scholar
• Garcia , J. , Fernandez , S. , Ferrero , M. , Sanghvi , Y. S. and Gotor , V. A. 2004 . Mild, efficient and regioselective enzymatic procedure for 5′‐O‐benzoylation of 2′‐deoxynucleosides . Tetrahedron Lett. , 45 : 1709 – 1712 .
   Web of Science ®Google Scholar
• Bhat , B. and Sanghvi , Y. S. 1997 . A mild and highly selective N‐benzoylation of cytosine and adenine bases in nucleosides with N‐benzoyltetrazole . Tetrahedron Lett. , 38 : 8811 – 8814 .
   Web of Science ®Google Scholar
• Paquette , L. A. 1995 . Encyclopedia of Reagents for Organic Synthesis Edited by: Paquette , L. A. Vol. 3 , 2020 – 2024 . New York : John Wiley & Sons .
   Google Scholar
• Koenig , K. E. and Weber , W. P. 1974 . Synthesis of benzoyl cyanides by phase transfer catalysis . Tetrahedron Lett. , : 2275 – 2278 .
   Google Scholar
• Pan , Z.‐W. , Ling , B. and Yao , Q. 2000 . Synthesis of benzoyl cyanide . Hunan Huagong , 30 : 16 – 17 . Chem. Abstr. 2001, 134, 328155
   Google Scholar
• Paquette , L. A. 1995 . Encyclopedia of Reagents for Organic Synthesis Edited by: Paquette , L. A. Vol. 1 , 60 – 62 . New York : John Wiley & Sons .
   Google Scholar
• Fox , J. J. and Miller , N. C. 1963 . Nucleosides XVI: further studies of anhydronucleosides . J. Org. Chem. , 28 : 936 – 941 .
   Web of Science ®Google Scholar
• Zhiwei , W. , Prudhomme , D. R. , Buck , J. R. , Park , M. and Rizzo , C. J. 2000 . Stereocontrolled synthesis of deoxyribonucleosides via photoinduced electron‐transfer deoxygenation of benzoyl‐protected ribo‐ and arabinonucleosides . J. Org. Chem. , 65 : 5969 – 5985 .
   Google Scholar
• Kierzek , R. , Ito , H. , Bhatt , R. and Itakura , K. 1981 . Selective N‐deacylation of N,O‐protected nucleosides by zinc bromide . Tetrahedron Lett. , 22 : 3761 – 3764 .
   Web of Science ®Google Scholar
• Reese , C. B. and Richards , K. H. 1985 . Reaction between nucleoside base residues and the phosphorylating agent derived from 1‐hydroxybenzotriazole and 2‐chlorophenyl phosphorodichloridate . Tetrahedron Lett. , 26 : 2245 – 2248 .
   Web of Science ®Google Scholar
• Matsuda , A. , Shinozaki , M. , Suzuki , M. , Watanabe , K. and Miyasaka , T. 1986 . A convenient method for the selective acylation of guanine nucleosides . Synthesis , : 385 – 386 .
   Web of Science ®Google Scholar
• Shimomura , N. , Matsutani , T. and Mukaiyama , T. 1994 . Stereoselective syntheses of β‐D‐ribonucleosides catalyzed by the combined use of silver salts and diphenyltin sulfide or Lawesson's reagent . Bull. Chem. Soc. Jpn , 67 : 3100 – 3106 .
   Web of Science ®Google Scholar
• Leonard , N. J. and Laursen , R. A. 1963 . The synthesis of 3‐β‐D‐ribofuranosyladenine . J. Am. Chem. Soc. , 85 : 2026 – 2028 .
   Web of Science ®Google Scholar
• Nishino , S. , Takamura , H. and Ishido , Y. 1986 . Regioselective protection of carbohydrate derivatives, Part.20: Simple, efficient 2′‐O‐deacetylation of fully acylated purine and pyrimidine ribonucleosides through tert‐butoxide . Tetrahedron , 42 : 1995 – 2004 .
   Web of Science ®Google Scholar