Synthesis of 2‐deoxyinosadiamines‐1,3 including 2‐deoxystreptamine

Abstract

Hydrogenation of 4,6-dinitropyrogallol over a rhodium-platinum catalyst yielded 2-deoxy-cis-inosadiamine-l, 3 as the main product. This was converted into 2-deoxy-epi-inosadiamine-l,3 by catalytic oxidation followed by transdirecting reduction. From the epi-isomer, 2-deoxystreptarnine was prepared by a similar oxidation/reduction procedure.

The Interplay of Hydrogen Bonding and Multiple Metal Binding – A New Cyclic Polyaminopolyalcohol Ligand as Building Block for the Construction of Microporous, Supramolecular Networks

“…The tachol, daci5a and ddci5b ligands were prepared by hydrogenation of P2 , P3 11a and P4 11b (5 bar H 2 , 20–45 °C, aqueous H 2 SO 4 ) using a Pt/Rh‐on‐C catalyst (see Supporting Information). Caution!…”

“…50 % daci · H 2 SO 4 ), which was purified by recrystallization. Although the resulting product still contained some 10 % of byproducts,5a it could be used for the synthesis of C3 : 1.17 g of this material was dissolved in H 2 O and deprotonated on an anion exchange resin (Dowex 2‐X8, OH‐form). CuSO 4 · 5H 2 O (530 mg, 2.1 mmol) was added.…”

“…Cyclohexane-based PAPA ligands have not received wide attention, although they can be readily obtained by stereospecific hydrogenation of aromatic precursors (Scheme 1). [5] Metal binding of 1,3,5-triamino-1,3,5-trideoxy-cis-inositol (taci) with its four distinct binding sites 31…”