Phosphonate-free phosphorylation of alcohols using bis-(tert-butyl) phosphoramidite with imidazole·hydrochloride and imidazole as the activator

Tetrahedron Letters

Volumn 52, Issue 28, 2011, Pages 3625-3629

  Haché, Bruno ^a   Brett, Lisa ^a   Shakya, Sagar ^a  

^a ARRAY BIOPHARMA INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BENZYL ALCOHOL; BIS(TERT BUTYL)PHOSPHORAMIDITE; IMIDAZOLE; PHENOL; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDOUS ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; PHOSPHORYLATION; STOICHIOMETRY;

EID: 79958263571     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.020     Document Type: Article

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21. For mechanistic considerations: With tetrazole, DPPA was also used as a phosphoramidite equivalent: S.-B. Chen, Y.-M. Li, X.-Z. Luo, G. Zhao, B. Tan, and Y.-F. Zhao Phosphorus, Sulfur Silicon Relat. Elem. 164 2000 277
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27. The commercial alcohol was 47% pure by HPLC.
28. Literature precedents, mostly in patents often purify by prep-HPLC and no product distribution data are available.
29. Scifinder® search of the N,N-di-alkyl-bis-tert-butyl phosphoramidite as a reagent returned >100 references, all of the references were using 1H-tetrazole as the activator. Three exceptions, pyridine·HCl (WO 2001040236, no phosphonate discussion); 1,2,3-triazole (WO 2001074369 and WO 2001074368, no phosphonate discussion) and pyridine·HCl + pyridine (phosphonate discussion with vague product distribution details); pyridine·HCl giving phosphonate by-product (Barnwell, N.; Cheema, L; Cherryman, J.; Dubiez, J; Howells, G.; Wells, A. Org. Process Res. Dev. 2006, 10, 644); Pyridine·HCl and Pyridine·HCl/imidazole. (no phosphonate discussion, rather O,N selectivity): Kato, Y.; Oka, N.; Wada, T. Tetrahedron Lett. 2006, 47, 2501; Imidazolium Trifluoroacetate (no phosphonate discussion): Gomez, C.; Chen. J.; Wang, S. Tetrahedron Lett. 2009, 50, 6691-6692.
30. In some cases, less sodium thiosulphate is necessary to prevent decomposition of the crude phosphate product.
31. In some cases, multiple chromatographies were required to remove the N,N-diisopropyl bis-tert-butyl phosphoramidate: