Reductive cleavage of N-O bonds using samarium(II) iodide in a traceless release strategy for solid-phase synthesis

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1349-1352

  Myers, Rebecca M ^a   Langston, Steven P ^a   Conway, Simon P ^a   Abell, Chris ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000966664     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0055162     Document Type: Article

References (31)

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24. A procedure for substitution measurement of Fmoc resins is given in the following: Bennett, W. D.; Christenden, J. W. Advanced Chemtech Handbook of Combinatorial and Solid-Phase Organic Chemistry; 1998: p 330.
25. Abbreviations: dichloromethane (DCM), N,N-diisopropylethylamine (DIPEA), N-hydroxybenzotriazole hydrate (HOBt), diisopropylcarbodiimide (DIC), diisopropyl azodicarboxylate (DIAD). 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
26. HPLC purity at 254 nm unless noted otherwise.
27. HPLC purity at 220 nm.
28. Purity determined from the peak area in the LC trace over UV range 215-330 nm.
29. 2). Anal. Calcd: N, 1.74. Found: N, 1.95. Loading 1.18 mmol/g (based on N anal.). Yield 91% (based on N analysis).
30. R 14.4 min, 99.2% (254 nm, TSK gel Oligio DNA RP; solvent A acetonitrile + 0.1% TFA, solvent B milliQ water + 0.1% TFA, gradient 5-95% solvent A over 15 min).
31. R 5.0 min. purity 99% estimated by LC area (UV 215-330 nm).