Replacement of OH with H, N, and

For a commentary on the mechanism of this reaction, in particular the source of the hydrogen that replaces the OH group, see Grynszpan, F. Biali, S. E. J. Phys. Org. Chem. 1992, 5,155. 

Replacement of OH with NH2 has been attempted in a stepwise fashion via the A,C-dihydroxy compound 95b, but treatment with NO2BF4 results in oxidation (see Section 5.3.2) rather than nitration. A more successful approach involves treatment of the diphosphate ester 168 (Y = OPO(OEt)2 = OH) with KNH2 in NH3, which gives a mixture from which the monoamine 168b and diamine 168c can be isolated in 44% and 8% yield, respectively. Still 

Ohseto, F. Murakami, H. Araki, K. Shinkai, S. Tetrahedron Lett. 1992, 33,1217. 

One group of workers initially reported the monoamine 168b as the trihydroxy compound 

Replacement of OH with SH has been accomplished by means of the New-man-Kwart procedure which involves the reaction sequence  

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