Acids aldaric

There are four pentaric acids and ten hexaric acids  

Pentaric acids (sometimes known as hydroxyglutaric) ribaric (meso), xylaric (meso), and D- and L-arabinaric (d- and L-lyxaric). 

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. 

D-Glucaric acid was reported to occur as the magnesium salt in the sap of Ficus elastica,250 and 3-deoxy-mawzo-heptaric acid (cerheptaric acid) has been found to be widely distributed in the Cereus and Trichocereus genera of the Cactaceae family.251 

D-Glucaric acid is readily prepared by oxidation of D-glucose or starch with nitric acid, as described by Bose et al.,252 who also developed a 

The formation of D-glucaric acid by platinum-catalysed oxidation of D-gluconic acid has been noted in the previous section. Mono- and per-allyl ether derivatives of xylaric and galactaric acids have been prepared by treating the aldaric acid with allyl alcohol in the presence of an appropriate acid catalyst. Diallyl 3-0-allyl-2,4-0-methylenexylarate was obtained in good yield when 2,4-0-methylenexylaric acid reacted with allyl bromide in the presence of alkali. The reaction of 2,3,4-tri-O-acetylxylaryl dichloride with diazomethane has been mentioned in Chapter 7. 

Lapenko, B. I. Mikhant ev, and A. I. Slivkin, Izvest. Vyssh. Uchebn. Zaved., Khim. i khim. Tekh-noi, 1977, 20, 659 Chem. Abs., 1977, 87, 168 313z). 

The synthesis of 1,6-dlamino-l,6-dideoxygalactltol from dimethyl galactarate by t-butyldimethylsllylation, ammonolysls and dlborane 

Mamedov, G.L.Vidovich, and G.A.Bogdanovskii, Vestn. Mosk. Univ., Ser. 2t 

Potapov, V.l.Krupenskii, and H.I.Alieva, React. Kinet. Catal. Lett., 

Banner, A.J.Laurenzano, euid L.carozza, Org. Synth., 1985, 63, 

Vekemans, J.Boerekamp, E.F.Godefroi, eUid G.J.F.CSiittenden, Reel. 

spectra of a series of trihydroxyglutaric acid derivatives (286) have shown that the hydrogens attached to C-2 and C-4 in the D- and L-arabino isomers are non-equivalent, whereas those of the symmetrical ribo and xylo isomers are equivalent. Vicinal coupling constants were used to predict the following major conformations ribo- 2S6) (sickle), xylo-(2B6) (sickle), and arabino- 2%6) (planar zig-zag). 

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.  

7-Amino-2,6-anhydro-7-deoxy-L- /ycero-L- a/ac/o-heptonic acid (290) has been synthesized by way of selective ring-opening of 3,4,5-tri-0-acetyl-2,6-anhydro-D- /yceru-L-wflt no-heptaric anhydride (291) with ammonia. Daucic acid, a sugar acid present in wheat, sugar beet, and tobacco, etc.y has been identified as 2,6-anhydro-3-deoxy-D-x y/o-hept-2-enaric acid (292).  

Aldaric acids obtained by treatment of 4-0-methyl-D-glucuronic acid with alkali are reported in the following section. 

H And n.m.r. have been used to determine the preferred solution 

Cestric acid, isolated from Oestrum evanthes is an equilibrated 

Galactarlc acid chloride tetra-acetate, condensed with anthranilic acid followed by dehydration, gave the oxazlnone (8), 

The identity of the first naturally occurring saccharlnlc acid lactone to be detected (de Pascual Teresa et al., Tetrahedron Lett., 1980, 2], 1359) has been confirmed as 2-C-methyl-D-erythrono-l,4- 

Methyl (methyl 3-deoxy-a-D-arablno-2-heptulopyranosld)onate (13) 

---

The reaction of aldoses with nitric acid leads to the formation of aldaric acids by oxidation of both the aldehyde and the terminal primary alcohol function to carboxylic acid groups Aldaric acids are also known as saccharic acids and are named by substi tutmg aric acid for the ose ending of the corresponding carbohydrate... 

Like aldonic acids aldaric acids exist mainly as lactones... 

Another hexose gives the same aldaric acid on oxidation as... 

Aldaric acid (Section 25 19) Carbohydrate in which car boxyhc acid functions are present at both ends of the chain Aldanc acids are typically prepared by oxidation of aldoses with nitnc acid... 

Oxidation of tiie caibon atoms at both ends of the carbon chain produces an aldaric acid. That made from D-galactose is galactaric acid [526-99-8] a... 

Oxidation of (—)-arabinose with warm nitric acid gave an optically active aldaric acid. 

Both (-l-)-glucose and (-l-)-mannose were oxidized to optically active aldaric acids with nitric acid. 

There is another sugar, (-l-)-gulose, that gives the same aldaric acid on oxidation as does (-l-)-glucose. 

Monosaccharides can be oxidized enzymatically at C-6, yielding uronic acids, such as D-glucuronic and L-iduronic acids (Figure 7.10). L-Iduronic acid is similar to D-glucuronic acid, except for having an opposite configuration at C-5. Oxidation at both C-1 and C-6 produces aldaric acids, such as D-glucaric... 

If a more powerful oxidizing agent such as warm dilute HN03 is used, an aldose is oxidized to a dicarboxylic acid, called an aldaric acid. Both the —CHO group at Cl and the terminal -CH2OH group are oxidized in this reaction. 

Which of the other six d aldohexoses yield optically active aldaric acids on oxidation, and which yield optically inactive (meso) aldaric acids (See Problem 25.19.)... 

Much of the chemistry of monosaccharides is the familiar chemistry of alcohols and aldehydes/ketones. Thus, the hydroxyl groups of carbohydrates form esters and ethers. The carbonyl group of a monosaccharide can be reduced with NaBH4 to form an alditol, oxidized with aqueous Br2 to form an aldonic acid, oxidized with HNO3 to form an aldaric acid, oxidized enzymatically to form a uronic acid, or treated with an alcohol in the presence of acid to form a glycoside. Monosaccharides can also be chain-lengthened by the multistep Kiliani-Fischer synthesis and can be chain-shortened by the Wohl degradation. 

Which of the eight f> aldohexoses give the same aldaric acids as their i. enantiomers ... 

Which of the other three n aldopentoses gives the same aldaric acid as D-lyxose ... 

Compound A is a D aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischei chain extension, A is converted into C and D C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid F. What are the structures of A-F ... 

Aldaric acid (Section 25.6) The dicarboxylic acid resulting from oxidation of an aldose. 

Thedicarboxylic acids formed from aldoses by replacement of both terminal groups (CHO and CH2OH) by carboxy groups are called aldaric acids (see 2-Carb-23). 

The parent that includes the functional group most preferred by general principles of organic nomenclature [13,14], If there is a choice, it is made on the basis of the greatest number of occurrences of the most preferred functional group. Thus aldaric acid > uronic acid/ketoaldonic acid/aldonic acid > dialdose > ketoal-dose/aldose > diketose > ketose. 

Names of individual aldaric acids are formed by replacing the ending -ose of the systematic or trivial name of the parent aldose by -aric acid . Choice between possible names is based on 2-Carb-2.2.2. 

To the names of aldaric acids that are symmetrical, which therefore have no D- or L- prefix, the prefix meso- may be added for the sake of clarity. Examples mero-erythraric acid, meso-ribaric acid, meso-xylaric acid, meso-allaric acid, meso-galactaric acid. 

The D or L prefix must however be used when a meso-aldaric acid has become asymmetric as a result of substitution. 

There are distinct correlations between the mechanism of formation of compound 43, the eliminations frequently observed with derivatives of aldaric acids, and the reducing power of alkyl D-glucofuranosidurono- and l,2-0-alkylidene-a-D-glucofuranurono-6,3-lactones toward complexed copper(II) solutions. These phenomena are discussed in Section VII. 

Figure 9.11 Oxidation products of glucose. Gluconic acid is an aldonic acid formed when the aldehyde group is oxidized. Glucuronic acid, a uronic acid, is a result of oxidation of the primary alcohol group. When both the aldehyde and the primary alcohol groups are oxidized, glucaric acid is formed, which is an aldaric acid.

Aldaric acids are formed when stronger oxidizing conditions are employed, such as nitric acid, when both the aldehyde and primary alcohol groups are oxidized. 

---