Selective synthesis of phosphate monoesters by dehydrative condensation of phosphoric acid and alcohols promoted by nucleophilic bases

Organic Letters

Volumn 7, Issue 10, 2005, Pages 1999-2002

  Sakakura, Akira ^a   Katsukawa, Mikimoto ^a   Ishihara, Kazuaki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BASE; ESTER DERIVATIVE; IMIDAZOLE DERIVATIVE; NUCLEIC ACID BASE; PHOSPHATE; PHOSPHORIC ACID; RIBONUCLEOSIDE DERIVATIVE; TRIBUTYLAMINE;

ARTICLE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ALCOHOLS; IMIDAZOLES; MOLECULAR STRUCTURE; PHOSPHATES; PHOSPHORIC ACIDS; PYRIDINES; RIBONUCLEOSIDES;

EID: 19544374511     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0504796     Document Type: Article

References (11)

1. For reviews, see: (a) Hayakawa, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon: Oxford, 1991; Vol. 6, pp 601-630.
2. (b) Slotin, L. A. Synthesis 1976, 737.
3. Honjo, M.; Furukawa, Y.; Kobayashi, K. Chem. Pharm. Bull. 1966, 14, 1061.
4. Although the 5′-monophosphate of 2′,3′-O-isopropylidene uridine (9) has been synthesized in 58% yield using the method of ref 2, 2′,3′-O-isopropylidene adenosine (10), cytidine (11), and guanosine (12), which are thermally unstable, have been converted to their 5′-monophosphates in respective yields of 38, 39, and 46%.
5. Ishihara, K.; Kosugi, Y.; Akakura, M. J. Am. Chem. Soc. 2004, 126, 12212.
6. 1H NMR.
7. 7) might also be a good phosphorylating agent for alcohols. However, Honjo et al. reported that the reaction of 2′,3′-O-isopropylidene inosine with pyrophosphoric acid gave its phosphate monoester (64%) along with its pyrophosphate monoester (21%) as a byproduct (ref 2).
8. 4), see: Imai, K.; Fujii, S.; Takanohashi, K.; Furukawa, Y.; Masuda, T.; Honjo, M. J. Org. Chem. 1969, 34, 1547.
9. For the phosphramidite method, see: (a) Hayakawa, Y.; Kataoka, M. J. Am. Chem. Soc. 1998, 120, 12395.
10. (b) Sekine, M.; Ohkubo, A.; Seio, K. J. Org. Chem. 2003, 68, 5478.
11. For the H-phosphonate method, see: Wada, T.; Sato, Y.; Honda, F.; Kawahara, S.; Sekine, M. J. Am. Chem. Soc. 1997, 119, 12710.