An Efficient Synthesis of 3′‐Amino‐3′‐deoxyguanosine from Guanosine
- 26 March 2003
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 86 (3) , 703-710
- https://doi.org/10.1002/hlca.200390069
Abstract
3′‐Amino‐3′‐deoxyguanosine was synthesized from guanosine in eight steps and 58% overall yield. The 2′,3′‐diol of 5′‐O‐[(tert‐butyl)diphenylsilyl]‐2‐N‐[(dimethylamino)methylidene]guanosine was reacted with α‐acetoxyisobutyryl bromide and treated with 0.5n NH3 in MeOH to yield 9‐{2′‐O‐acetyl‐3′‐bromo‐5′‐O‐[(tert‐butyl)diphenylsilyl]‐3′‐deoxy‐β‐D‐xylofuranosyl]‐2‐N‐[(dimethylamino)methylidene]guanine, which was reacted with benzyl isocyanate, NaH, and then 3.0n NaOH, and finally with Pd/C (10%) and HCO2NH4 in EtOH/AcOH to afford 3′‐amino‐3′‐deoxyguanosine.Keywords
This publication has 33 references indexed in Scilit:
- A phosphoramidate substrate analog is a competitive inhibitor of the Tetrahymena group I ribozymeChemistry & Biology, 2000
- Replacement of the Negative Phosphodiester Linkages of DNA by PositiveS-Methylthiourea Linkers: A Novel Approach to Putative Antisense AgentsJournal of the American Chemical Society, 1998
- Preparation of 2'-O-(.beta.-Cyanoethyl phosphoramidites) of 3'-Deoxycytidine and 3'-Deoxyguanosine and Their Use for Solid-Phase Synthesis of Oligodeoxynucleotides Containing 2',5'-Phosphodiester LinkagesThe Journal of Organic Chemistry, 1994
- Achiral internucleoside linkages: CH2-CH2-NH and nH-CH2-CH2 linkagesBioorganic & Medicinal Chemistry Letters, 1993
- Nucleic Acid Related Compounds. LXXXI. Efficient General Synthesis of Purine (Amino, Azido, and Triflate)-Sugar NucleosidesNucleosides and Nucleotides, 1992
- Stereospecific Synthesis of β-D-Xylofuranosides of Adenine and GuanineSynthesis, 1985
- Aminonucleoside, X. Über die Synthese von 3′‐Amino‐3′‐desoxyguanosin, 3′‐Amino‐3′‐desoxyguanosin‐5′‐monophosphat und seinem 3′,5′‐CyclophosphatEuropean Journal of Organic Chemistry, 1982
- Ribosome-catalysed reaction of puromycin with a formylmethionine-containing oligonucleotideJournal of Molecular Biology, 1967
- Studies on Synthetic Nucleosides. I. Trimethylsilyl Derivatives of Pyrimidines and Purines.CHEMICAL & PHARMACEUTICAL BULLETIN, 1964
- The α- and β-D-Xylofuranose Tetrabenzoates and Certain Other Derivatives of D-XyloseJournal of the American Chemical Society, 1953