328 INOSITOLS 



NH, 



H,N 



XVII XVIII 



2-Amino-2-desoxy-m2/o-inositol Aminodesoxyscyllitol 



(TO2/o-Inosamine-2) (scyZZo-Inosaniine) 



through reference to the corresponding inositol, the w?/o-inositol relative, 

 XVII, being called 2-amino-2-desoxy-m?/o-inositol (or w?/o-inosamine-2), 

 while XVIII is simply aminodesoxyscyllitol (or sc;/Z/o-inosamine). The 

 reduction of nitrogenous derivatives of DL-2-keto-ept-inositol (XIII, XIV) 

 gives two enantiomorphic pairs of inosamines: DL-2-amino-2-desoxy-ep2- 

 inositol (DL-epi-inosamine-2, XIX-XX) and DL-4-amino-4-desoxy-m2/o-in- 

 ositol (DL-m?/o-inosamine-4, XXI-XXII). One of these compounds was 

 made by Carter and his coworkers.^^ The other has been synthesized by 

 Rieke et al}^ The methods of synthesis (cf. Anderson and Lardy^^) and 

 properties of the compounds indicate that the compound prepared by Carter 

 et al}^ (and designated EA) is DL-ep^-inosamine-2 (XIX-XX), and that 

 prepared by Rieke et alr^ is DL-m?/o-inosamine-4 (XXI-XXII). 



The antibiotic, streptomycin, contains a diamino didesoxyinositol, which 

 has been given the trivial name, streptamine. Previous evidence indicated 

 that streptamine has the configuration shown in XXIII. ^^ Wintersteiner 



41/ \|1 2 



XIX XX 



D-2-Amino-2-desoxy-epi-inositol L-2-Amino-2-desoxy-epi-inositol 



(D-epi-Inosamine-2) (L-epi-Inosamine-2) 



1 2 



P 3- 



5 4/ H,N 



NHs 

 XXI XXII 



.D-4-Amino-4-desoxy-w2/o- inositol L-4-Amino-4-desoxy-m!/o-inositol 

 (D-m2/o-Inosamine-4) (L-7«!/o-Inosamine-4) 



H2N 



NH2 

 XXIII 



1 ,3-Diamino- 1 ,3-didesoxyscyllitol 



21 H. Rieke, H. A. Lardy, and L. Anderson, J. Am. Chem. Soc. 75, 694 (1953). 



22 M. L. Wolfrom, S. M. Olin, and W. J. Polglase, J. Am. Chem. Soc. 72, 1724 (1950). 



