81602-08-6Relevant academic research and scientific papers
Streptamine from Benzene - An Efficient Synthesis of cis-Inosadiamines-(1,3) and cis-Deoxyinosadiamines-(1,3)
Schwesinger, Reinhard,Fritsche, Wolfram,Prinzbach, Horst
, p. 946 - 966 (2007/10/02)
Efficient syntheses for cis-inosadiamines-(1,3) and cis-deoxyinosadiamines-(1,3) start out from 1,2-anhydro-4,6-dideoxy-4,6-hydrazo-myo-inositol (14a), which is selectively produced from cis-"benzene trioxide" (1) and hydrazine.Under hydrolysis conditions within wide pH-limits aziridine formation (15a) prevails; only in strongly alkaline solution uniform epoxide opening (C-2) occurs yielding the precursor (5a) of the 2,4-diamino-2,4-dideoxy-chiro-inositol (6a).By "masking" the hydrazo bridge (19a, 21) C-4-substitution is enforced (20a, 22) paving the way to 1,3-diamino-1,3-dideoxy-scyllo-inositol (2, steptamine), which is obtained in reasonable yields.Hydrazine (24a), phenylmethanethiol (26a), hydrochloric and hydrobromic acid (30a, d) add regiospecifically to 14a at C-4. 1,3-Diamino-1,3,5-trideoxy-scyllo-inositol (3,5-deoxystreptamine) and DL-2,4-diamino-1,2,4-trideoxy-chiro-inositol (33a) are quantitatively formed in the catalytic hydrogenation of 14a in neutral to acidic and basic solution, resp.
