755690-05-2Relevant academic research and scientific papers
Polyfunctionalised Cyclohexanes from Dianhydroinositols. cis-1,3(1,4)-Inosadiamines from Benzene
Schubert, Juergen,Keller, Reinhold,Schwesinger, Reinhard,Prinzbach, Horst
, p. 2524 - 2545 (2007/10/02)
The preparative value of the dianhydroinositols 4 - 6, which are readily available from benzene, for the total synthesis of cis-1,4- and cis-1,3-disubstituted cyclohexanetetrols is demonstrated.With monovalent reagents (H2O, HI, NaN3, NH2NH2) the twofold epoxide opening proceeds regioselectively (1,4-disubstitution) yielding the muco- and chiro-cyclohexane derivatives 9, 17, and 26.With hydrazine and N,N'-dimethylhydrazine as 1,2-dinucleophiles the cis-1,3-inosadiamines 7 g (5-epistreptamine) and 16 g, j (2-epistreptamine, actinamine) are obtained from 4/5 in good yields (75 - 90percent).From the less symmetrical 6, however, only the mixture of 25 g (streptamine) and 27 g is produced in modest yield (ca. 50percent).The epoxide opening reactions starting from 4 - 6 are kinetically so similar that a selective opening is not possible.
