Novel phosphate ester-linked resins: The solid-phase generation of phenyl phosphate-containing compounds for SH2 inhibition

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3435-3438

  Metcalf III, Chester A ^a   Vu, Chi B ^a   Sundaramoorthi, Raji ^a   Jacobsen, Virginia A ^a   Laborde, Edgardo A ^a,b   Green, Jeremy ^a,c   Green, Yinka ^a,d   Macek, Karina J ^a   Merry, Taylor J ^a   Pradeepan, Selvi G ^a   Uesugi, Mayumi ^a   Varkhedkar, Vaibhav M ^a   Holt, Dennis A ^a  

^a ARIAD PHARMACEUTICALS INC   (United States)

^b Terrapin Technologies Inc   (United States)

^c VERTEX PHARMACEUTICALS   (United States)

^d Astra Hassle   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE; PHOSPHONIC ACID ESTER; PHOSPHORAMIDIC ACID; RESIN; TYRAMINE;

ARTICLE; CHEMICAL STRUCTURE; DRUG RESEARCH; MOLECULAR STABILITY; PROTEIN PROTEIN INTERACTION; SIGNAL TRANSDUCTION; SOLID PHASE EXTRACTION;

EID: 0032554979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00586-3     Document Type: Article

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12. 2O).
13. 2O, etc.) and therefore require greater care when handled as compared to analogous intermediates used in oligonucleotide synthesis.
14. The loading capacities of resins 4a-c/7g-i were determined by spectrophotometric measurement of the cleaved Fmoc group from a pre-dried/weighed resin sample.
15. -) prior to weighing.
16. 9
17. -3 mol x MW added to resin)] for Wang resin 1.15 mmol/g loading.
18. 2O/MeOH.
19. 2O (2:1) conditions (2h) without any measurable loss in loading capacity.
20. 3, CuO, pyr, 140 °C) between 4-benzyloxyphenol and the appropriately substituted cyanophenyl bromide.
21. +): m/z 350, M+H] as determined by LCMS of the crude cleaved product.
22. Lunney, E. A.; Para, K. S.; Rubin, J. R.; Humblet, C.; Fergus, J. H.; Marks, J. S.; Sawyer, T. K. J. Am. Chem. Soc. 1997, 119, 12471.