Copper(II)nitrate catalyzed regioselective protection of primary alcohols with 4,4′-dimethoxytrityl and 2,7-dimethyl-9-phenyl xanthen-9-yl groups in nucleosides and carbohydrates

References

• (a) Tripathi, S.; Misra, K.; Sanghvi, Y. S. One-pot Synthesis of TBMPS (Bis [tert-Butyl)-1 Pyrenylmethyl-Silyl) Chloride as a Novel Fluorescent Silicon-Based Protecting Group for Protection of 5′-OH Nucleosides and its Use as Purification Handle in Oligonucleotide Synthesis. Nucleosides, Nucleotides Nucleic Acids 2005, 24, 1345.
   PubMed Web of Science ®Google Scholar
  (b) Day, R. T.; Williams, D.; Soriano, P.; Sanghvi, Y. S. Large-Scale Synthesis of 5′-O-Pixyl Protected 2′-Deoxynucleosides useful for Oligonucleotide Synthesis. Nucleosides, Nucleotides Nucleic Acids 2005, 24, 1135.
   PubMed Web of Science ®Google Scholar
  (c) Oka, N.; Sanghvi, Y. S.; Theodorakis, E. A. 3,3-Oxybis(4′,4′′-dimethoxytrityl chloride) (O-DMT-Cl): Synthesis and application of a novel bifunctional protecting group. Bioorg. & Med. Chem. Letts. 2004, 14, 3241.
   PubMed Web of Science ®Google Scholar
  (d) Oka, N.; Sanghvi, Y. S.; Theodorakis, E. A. 1,2-Ethylene-3,3-bis(4,4′-Dimethoxytrityl Chloride) (E-DMT): Synthesis and. Applications of a Novel Protecting Reagent. Synlett. 2004, 823.
   Web of Science ®Google Scholar
  (e) Wen, K.; Chow, S.; Sanghvi, Y. S.; Theodorakis, E. A. Synthesis of 2′-O-Methoxyethylguanosine Using a Novel Silicon-Based Protecting Group. J. Org. Chem. 2002, 67, 7887.
   PubMed Web of Science ®Google Scholar
  (f) Srishylam, P.; Raji Reddy, A.; Banerjee, S.; Penta, S.; Sanghvi, Y. S. DDQ mediated Regiospecific Protection of Primary Alcohol and Deprotection Under Neutral Conditions: Application of New p-Methoxy Benzyl-Pixyl ether as Reagent of Choice for Nucleoside Protection. Tetrahedron Letts. 2017, 58, 2588.
   Web of Science ®Google Scholar
  (g) Matteo, A.; Gaspare, B.; Alfonso, I.; Marialuisa, S. Mild Benzhydrylation and Tritylation of Saccharidic Hydroxyls Promoted by Acid Washed Molecular sieves. Tetrahedron Letts. 2003, 44, 3733.
   Web of Science ®Google Scholar
• (a) Schaller, H.; Weimann, G.; Lerch, B.; Khorana, H. G. Studies on Polynucleotides. XXIV. The Stepwise Synthesis of Specific Deoxyribopolynucleotides (4). Protected Derivatives of Deoxyribonucleosides and New Syntheses of Deoxyribonucleoside-3″ Phosphates. J. Am. Chem. Soc. 1963, 85, 3821.
   Web of Science ®Google Scholar
  (b) Zekri, N.; Alamdari, R. F.; Nezhad, A. K. A Solvent Free and Selective Method for the Preparation of Triphenylmethyl Ethers of Alcohol and Nucleosides. Bull. Chem. Soc. Ethiop. 2010, 24, 299.
   Web of Science ®Google Scholar
  (c) Agarwal, K. L.; Yamazaki, A.; Cashion, P. J.; Khorana, H. G. Chemical Synthesis of Polynucleotides. Angew. Chem. Int. Ed. 1972, 11, 451.
   PubMed Web of Science ®Google Scholar
• Banerjee, S.; Srishylam, P.; Rajendra Prasad, S.; Migawa, M. T.; Swayze, E. E.; Sanghvi, Y. S. Scalable Synthesis of Substituted 2,7-Dimethyl-9-Phenylxanthen-9-ol (DMPx-OH): Useful for the Preparation of Crystalline 5′-O-DMPx-Protected Nucleosides. Tetrahedron Lett. 2012, 53, 4669.
   Web of Science ®Google Scholar
• Raji Reddy, C.; Rajesh, G.; Balaji, S. V.; Chethan, N. Tris(Pentafluorophenyl)Borane: A Mild and Efficient Catalyst for the Chemoselective Tritylation of Alcohols. Tetrahedron Lett. 2008, 49, 970.
   Web of Science ®Google Scholar
• (a) Jyothi, Y.; Mahalingam, A. K.; Ilangovan, A.; Sharma, G. V. M. Alternative Reagents for the Tritylation of Alcohols. Syn. Comm. 2007, 37, 2091.
   Web of Science ®Google Scholar
  (b) Lundquist, J. T.; Satterfield, A. D.; Pelletier, J. C. Mild and Adaptable Silver Triflate-Assisted Method for Trityl Protection of Alcohols in Solution with Solid-Phase Loading Applications. Org. Lett. 2006, 8, 3915.
   PubMed Web of Science ®Google Scholar
• Misetic, A.; Boyd, M. K. The Pixyl (Px) Group: A Novel Photocleavable Protecting Group for Primary Alcohols. Tetrahedron Lett. 1998, 39, 1653.
   Web of Science ®Google Scholar
• Sproviero, M.; Katherine, M. R.; Witham, A. A.; Manderville, R. A. Utility of 5′-O-2,7-Dimethylpixyl for Solid-Phase Synthesis of Oligonucleotides Containing Acid-Sensitive 8-Aryl-Guanine Adducts. J. Org. Chem. 2014, 79, 692.
   PubMed Web of Science ®Google Scholar
• Sreedhar, B.; Radhika, P.; Neelima, B.; Chowdary, D. V. D. B.; Rao, M. V. B. FeCl3-Catalyzed Tritylation of Alcohols in Ionic Liquids. Syn. Commun. 2009, 39, 3785.
   Web of Science ®Google Scholar
• Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis. 2nd ed.; John Wiley and Sons: New York, 1999; pp 102–104.
   Google Scholar
• Das, B.; Mahendar, G.; Kumar, V. S.; Chowdhury, N. Chemoselective Deprotection of Trityl Ethers using Silica-Supported Sodium Hydrogen Sulfate. Tetrahedron Lett. 2004, 45, 6709.
   Web of Science ®Google Scholar
• Yadav, J. S.; Reddy, B. V. S. A Mild and Selective Cleavage of Tritylethers by Cerium (III) Chloride. Synlett 2000, 12, 1275.
   Google Scholar
• Pathak, A. K.; Pathak, V.; Seitz, L. E.; Tiwari, K. N.; Akhtar, M. S.; Reynolds, R. C. A Facile Method for Deprotection of Trityl Ethers using Column Chromatography. Tetrahedron Lett. 2001, 42, 7755.
   Web of Science ®Google Scholar
• Ravikumar, V. T.; Krotz, A. H.; Cole, D. L. Efficient Synthesis of Deoxyribonucleotide Phosphorothioates by the Use of DMT Cation Scavenger. Tetrahedron Lett. 1995, 36, 6587.
   Google Scholar
• Kicsak, M.; Bege, M.; Bereczki, I.; Csavas, M.; Herczeg, M.; Kupihar, Z.; Kovacs, L.; Borbas, A.; Herczegh, P. A three-Component Reagent System for Rapid and Mild Removal of O-, N- and S-Trityl Protecting Groups. Org. Biomol. Chem. 2016, 14, 3190.
   PubMed Web of Science ®Google Scholar