L-Mannaric acid

C2 symmetric diols having a L-mannaric acid backbone were developed as shown in Fig. 15 [185]. A series of fluoro-substituted Pi/Pj analogs (58) of these symmetrical diols were synthesized and tested with the aim of improving their anti-HIV activity. QSAR 67 [15] reported for the data showed that electron-releasing substituents on the two phenyl rings and the hydrophobic-ity of the molecule have a positive effect on the activity. Similar to QSAR 66,... 

Fig. 15 Design of C2-symmetric diols (L-Mannaric acid) (Reprinted with permission from [185]. Copyright 2001 American Chemical Society)...

Hexaric acids allaric (meso), formerly a//o-mucic galactaric (meso), formerly mucic D- and L-glucaric (l- and D-gularic), formerly D- and L-g/Mco-saccharic D- and L-mannaric, formerly D- and L-manno-saccharic D- and L-idaric, formerly D- and L-ido-saccharic and D- and L-altraric (d- and L-talaric), formerly D- and L-ta/o-mucic acid. 

Typically, condensations to polyamide (II), are carried out between an activated, i.e., esterified (diester, ester/lactone, dilactone) form of the aldaric acid (I), and a primary diamine in a polar protic solvent such as methanol at room temperature. Under those conditions any starting single ester form of a five or six carbon aldaric acid is rapidly converted to an equilibrium mixture of acyclic diester and ester/lactone forms. Dilactone, if formed at all, is present in only small amounts. The starting monomer esterified form(s) of the aldaric acid differ from one acid to an other. For example, the monomers of choice for L-tartaric acid (1) and weso-galactaric acid (4) are simple diesters, while for D-glucaric acid suitable monomers are ester/lactones, dilactone, or even the entire alcohol esterified mixture (10). Xylaric acid is also conveniently polymerized as its esterification mixture while the D-mannaric acid monomer is the 1,4 6,3-dilactone (13a). 

Kiely D.E., Chen. L., Lin T.-H., Synthetic poly hydroxy polyamides from galactaric, Xylaric, o-glucaric, and D-mannaric acids and aLkylenediamine monomers-Some comparisons, J. Polym. Sci. Part A Polym. Chem., 38, 2000, 594-603. 

A meso -compd., certain derivs. induce asymmetry. For stereoisomers see Glucaric acid, G-241, Allaric acid, A-74, Mannaric acid, M-23, Galactaric acid, G-2 and Idaric acid, I-l. Isol. from sporophylls of brown algae, various fruits and fungi. Used as 2% aq. soln. to form colour complexes with Fe, Co, Cr(/J7), Mn, U(F/). (pH 3-10). Cryst. Sol. alkalis spar. sol. H2O. 

Tetra-O-methyl-D-mannaric acid, M-23 L-Threaric acid, T-12... 

D-Mannose —> D-mannonic acid —> L-mannuronic acid mannaric acid... 

Oxidation of D-mannaric acid l,4 6,3-dilactone with potassium permanganate furnished the dienone (287), which was transformed into a series of pyrrole and other derivatives. The hydroxy-groups at C-2 and C-5 of D-mannaric acid l,4 6,3-dilactone could also be oxidized in turn to give (288) and (289) treatment of these products with hydrogen bromide in acetic acid-acetic anhydride introduced geminal bromo and acetyl groups at C-2 and at C-5, respectively." ... 

The problem now resolved into determining the configuration of C-4 for structures H and J (reaction 2.5). Fischer reasoned that because both D-glucaric acid and D-mannaric acid were optically active, the configuration of the OH group at C-4 had to be to the right (structure K below) because, if it were to the left, the aric acid of structure H would be optically inactive due to intramolecular symmetry (structure L, below). 

Tetra-O-methyl-D-mannaric and galactaric acids and their bis(pentachlorophenyl) esters have been prepared [99] as crystalline compounds, in good yields, from D-mannitol and galactitol, respectively. A new stereoregular fully sugar-based polyamide, analogous to Nylon 66, has also been prepared [99] by polycondensation of bis(pentachlorophenyl) 2,3,4,5-tetra-O-methyl-D-mannarate with l,6-diamino-l,6-dideoxy-2,3,4,5-tetra-<9-methyl-D-mannitol dihydrochloride [100]. 

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