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. Author manuscript; available in PMC: 2014 Feb 27.
Published in final edited form as: J Am Chem Soc. 2013 Feb 14;135(8):3121–3135. doi: 10.1021/ja310650n

Scheme 4.

Scheme 4

Addition of OH to C5 of T(−H)• yields T(5OH)• (5R and/or 5S). Subsequently, T(5OH)• is converted to various diastereomers of T(6OH)•. The R and S steroisomers of T(6OH)• can not be distinguished by ESR spectroscopy and only the axial and equatorial conformers can be distinguished on the basis of β C6-H HFCC values whereas for T(5OH)• only C6αH hyperfine coupling is experimentally observable and it is same (ca. 20 G) for R or S.