1,4-Diamino-2,3-diols

Asymmetric 1,4-diamino-2,3-diols. (S)-N-Cbz-amino aldehydes 2 undergo pina-eol homoeoupling in the presence of 1 to afford (1S,2R,3R,4S)-1,4 bis(Cbz-amino)-2,3-diols (3) in good yield and high diastcreosclcctivity. 

Das gleichzeitig gebildete vie. und gem. Diamino-diol wird bei der alkalischen Aufarbeitung untcr Rclro-al-dol-Addition zum Aldehyd aufgespalten,... 

In the meso-trick the same principle is applied [25]. A symmetric compound, in this case a meso compound, is submitted to selective hydrolysis. The asymmetric compound that is generated in this manner is obtained in 100% yield and ideally high optical purity (Scheme 6.8). Meso compounds with diamino, diol or diacid functions can be converted to chiral mono-esters or mono-amides, too, if the reaction is performed in organic solvents [22, 24, 27]. 

Hydroxylamines also react with nonsymmetrical aziridines under Lewis-acidic conditions to give products of nucleophilic attack at the less-substituted site. Thus, treatment of methyl aziridine 55 with A -/-butylhydroxylamine 56 and 20mol% boron trifluoride etherate provides the diamine derivative 57 in 77% yield <2001TL8243>. Fluoride ion is a powerful catalyst for the reaction of aziridines with the weakly nucleophilic />-toluenesulfonamide, a phenomenon which has been applied with advantage toward the preparation of protected diamino diol 59, a precursor to the aminocyclitol substructure (Scheme 17) <2001TL6433>. 

Nine chiral, tricyclic triquinphosphoranes (77a-i), have been prepared from chiral enantiopure diamino diols (76a-i) and their NMR data... 

This exercise indicated that the ends of the inhibitor were exposed, and that the solubility could be enhanced by modifying the end groups. One compound produced by this route entered clinical trials as an intravenous treatment. This compound had the basic diamino, diol structure but the X groups were as shown in Structure 4.8. 

A-Protection of 3-amino-1-propanol followed by tosylation gave (490) Scheme 5.115.). Treatment with A -benzyloxycarbonyl-1,4-diaminobutane in the presence of lithium bromide followed by a second butoxycarbonyl protection gave (491) which was debenzylated by hydrogenolysis and treated with 2,2-diethoxyacetic acid, 1-hydroxybenzotriazole and dicyclo-hexylcarbodi-imide to give (492). Careful acid hydrolysis gave the diamino diol (493). 

Library 1.13 Diamino-diol, -alcohol Size ca. 300 members Affiliation Abbott Laboratories [28] Year 1995... 

Wang, G.T., Li, S., Wideburg, N., Krafft, G.A. and Kempf, D.J., Synthetic chemical diversity Solid phase synthesis of libraries of C(2) symmetric inhibitors of HIV protease containing diamino diol and diamino alcohols cores, J. Med. Chem., 38 (1995) 2995-3002. 

A range of bis- and tris-spirocyclic cyclotriphosphazenes 182-187 containing bi-2-napthoxy, 2,2 -biphenoxy, 2,2-dimethyl-1,3-propane diamino, and 2,2-dimethyl-1,3-propane dioxy ligands have been prepared from the appropriate diamines and diols <2004POL979>. 

In contrast to NjPjCle, N4P4Q8 is extremely reactive towards difunctional reagents. This has led to the isolation of several decomposition products. Reactions with Af-methyl ethanolamine [87], 1,3-propane diol and 1,3-diamino propane afford mainly spiro products [138]. A detailed investigation on the reactions of N4P4CI8 with HO- CH2) -OH (n = 3, 4) has revealed that... 

Perhydro-diazocines 28, for the preparation of l,4-diamino-2,3-diol units that are the central structural elements in numerous biomaterials, were obtained from 1,3-cyclooctadiene, by reaction with diethyl azodicarboxylate (DEAD) to give the bridged 1,2-diazocine 103, which by ozonolysis gave the dialdehyde 104 that underwent... 

A 2- or 6-hydroxy-substituted purine can be prepared from the corresponding 4,5-diamino-pyrimidinol by cyclization with an acid, ester, ortho ester, or amide. If the ring closure is performed with reagents such as urea, alkyl chloroformates, urethanes, phosgene, and alkyl isocyanates, the 8-hydroxypurines are formed. Various xanthine and uric acid derivatives have been prepared by the condensation of 5,6-diaminopyrimidine-2,4-diols with formic acid. Purin-2-ol (1) was prepared by this route from 4,5-diaminopyrimidin-2-ol and ethyl orthoformate. ... 

The optimum catalyst for the reaction of 175 and cyclopentadiene was generated in-situ from one equivalent of the diol and two equivalents of ethyl aluminum dichloride. Presumably this generates a Lewis acid with two dichloroalkoxy aluminum groups per molecule of catalyst. The catalyst generated from diol 181 and one equivalent of diethylaluminum chloride is not very active, possibly because here the catalyst is a di-alkoxy aluminum chloride. The highest induction was observed for a catalyst generated from the diamino substituted diol 187, which was prepared from tartaric acid. 

Dimethy 1-4,4 -diamino-1,1 -biphenyl dihydrochloride was obtained from Professor Lorraine Deck at the University of New Mexico and used as received. Maleic anhydride was obtained from Eastman Kodak and p-aminobenzoic was obtained from National Starch. The other anhydrides, diols, and reagents were purchased from Aldrich Chemical. All reagents were used without further purification. The monomers were synthesized via a Schotten-Baumann type procedure using the appropriate acid chloride endcap and diamines or diols. Triethylamine was used as a scavenger for HC1. The monomers were recrystallized from appropriate solvents in yields of approximately 70%. 

Amino-7-phenylpyrimido[4,5- (]pyrimidine-2,4-diol (22) can be obtained by reacting 4,6-diamino-2-phenylpyrimidine-5-carboxamidc (21) with urea.110 The amide is prepared by hydrolysis of the corresponding pyrimidinecarbonitrile.109... 

Diphenyl isophthalate 3, 3w-Diamino-2,2-diphenyl-propan e-4, 4 -diol... 

This unusual annulation was reported with saxitoxin, 2,6-diamino-4- [(amino-carbonyl)oxy]methyl -3a,4,8,9-tetrahydro-l//,10/7-pyrrolo[l,2-c]-purine-10,10-diol (38a) isolated from tissue of a bullfrog and its derivatives, neosaxitoxin, 2,6-diamino-4- [(aminocarbonyl)oxy]methyl -3a,4,5,6,8,9-hexahydro-lf/,10//-pyr-rolo[l,2-c]purine-10,10-diol (38b) (91MI1)), gonyautoxin, 2,6-diamino-4- [(ami-nocarbonyl)oxy]methyl -3a,4,5,6,8,9-hexahydro-lf/,10/7-pyrrolo[l,2-c]purine-9,10, 10-triol (38c) (Scheme 9). Application of these compounds as local anaesthetics was published by Kohane (98MIP1). 

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