Hexono-1,4-lactone

Ethanolysis of 2,4-di-0-benzoyl-3,6-dideoxy-L-ara mo-hexono-l,5-lactone (92) afforded ethyl 2,4-di-0-benzoyl-3,6-dideoxy-L-araW/to-hexonate (93a). On being kept, compound 93a was slowly converted into 2,5-di-O-benzoyl-3,6-dideoxy-L-ara6mo-hexono- 1,4-lactone (94). This transformation involves O-4 — 0-5 benzoyl migration, with formation of ethyl 2,5-di-0-benzoyl-3,6-dideoxy-L-araA ohexonate (93b) as an intermediate (89). 

Pentono- and hexono-1,4-lactones yielded substituted arylhydrazides on treatment with m- and />-tolyl-, m- and p-methoxyphenyl, p-bromophenyl, and p-ethoxycarbonylphenyl-hydrazines (131). It was found that the rate of hydrazinolysis depends on the configuration of the aldonolactone, as well as on the aryl substituent on the hydrazine. 

Diisobutylaluminum hydride was also employed (153) for the reduction of 2,6-dideoxy-3-C-methyl-D-arabmo-hexono-1,4-lactone (121) to an antibiotic component, the branched-chain sugar evermicose (2,6-dideoxy-3-C-methyl-D-nrabmo-hexose, 122). The L-enantiomer of 122 (olivomycose, 125a), L-amicetose 125b, and 2,6-dideoxy-3-C-methyl-L-n Zw-hexose (l-... 

Simple syntheses of suitable monomers for nylon 5 and nylon 6 analogs, such as 5-amino-5-deoxyaldonic and 6-amino-6-deoxyaldonic acids (51, 54), has been achieved starting from unprotected o-pentono- and hexono-1,4-lactones [68, 69]. Saponification of 5- or 6-azido-D-aldonolactones ribo-, arabino-, xylo-, galacto-, manno-, compound types 49 and 52) provided the corresponding 5- or 6-azido-aldonic acid sodium salts (50, 53). A catalytic hydrogenation after or before treatment with acidic resin afforded compounds 51 and 54 in excellent overall yields (Scheme 16). 

If a polyol with a primary epoxide is treated with strong base, a rearrangement to the more stable secondary epoxide takes place, as observed by Payne [40]. If an unprotected bromodeoxyaldonolactone is treated with strong base a similar rearrangement may be expected. We found that if 6-bromo-2,6-dideoxy-D-arahzno-hexonolactone (3) (Scheme 5) was treated with 4 molar equivalents of potassium hydroxide, 2-deoxy-L-n bo-hexono-1,4-lactone (15) was isolated as the only product after work up [32]. 

Selective tosylation or mesylation of unprotected aldonolactones, to give the primary sulfonate only, seemed not to be possible since the 2-hydroxy group has about the same reactivity in these reactions as the primary one [28,29]. Selective di-O-tosylation was possible by treatment of aldonolactones with 2.2 mole equivalents of tosyl chloride to give 2,5-di-O-tosylated pentono- or 2,6-di-O-tosylated hexono-1,4-lactones [28]. The yields of crystalline ditosylates were high, when the OH-2 and OH-3 groups were cis- oriented and also cis to the side chain, and somewhat lower when they were both trans to the side chain. By this... 

The carbonyl frequency in the infrared spectrum provides a fairly characteristic method for differentiating between 1,4- and 1,5-lactones of aldonic acids. With few exceptions, the absorptions are in the range 1790-1765 and 1760 to 1725 cm-1, respectively.69 Configurational and conformational conclusions have been drawn from H and 13C NMR spectroscopy of aldonic acids and aldonolactones, using different correlation methods, enriched compounds, and shift reagents. For example, the solution conformation of aldono-1,4-lactones enriched with 13C at C-l have been determined on the basis of the coupling constants (homo and heteronuclear). In general, 0-2 is oriented quasi-equatorially due to stereoelectronic factors.36 Similar conclusions were made by Horton and Walaszek, who described the conformation of pentono- 1,4-lactones as an equilibrium between the 3E and forms.70 Conformations of D-hexono-1,4-lactones in solution have also been studied by NMR spectroscopy.70a The solution equilibrium of protected derivatives and their conformations have been described.71... 

Reaction of C-5 activated pentonolactones 13) and of 2,7-diactivated heptonolactones lib, 13) with ammonia gave in both cases 6-membered imino sugars by similar formation of epoxide intermediates (Scheme 4). The 6-bromo-2,6-dideoxy-D-anz6z> 0-hexono- 1,4-lactone gave by reaction with ammonia the 7-membered lactam 14) (Scheme 4). 

Dideoxy-L-arabino-hexono- 1,4-lactone 2-O-Methanosulfonyl-E21d, 4252 (En - An) Sulfuran(VI) (Dimethoxy-... 

Banfi, L, Beretta, M G, Colombo, L, Gennari, C, Scolastico, C, 2-Benzoylamino-2-deoxy-2-hydrox3miethyl-D-hexono-1,4-lactones synthesis from D-fructose and utilization in the total s3mthesis of thermoz3miocidin (myriocin), J. Chem. Soc., Perkin. Trans. 1, 1613-1619, 1983. 

Synonyms Vitamin C Acidum Antisorbutic vitamin Ascurbicum Cevitamic acid 2,3-Didehydro-L-threo-hexono-1,4-lactone E300 t-Ascorbic acid L-Xyloascorbic acid L-3-Ketothreohexuronic acid lactone... 

K. Bock, I. Lundt, and C. Pedersen, Base-catalyzed rearrangement of 6-bromo-3,6-dideoxyaldo-hexono-1,4-lactones, Acta Chem. Scand., B40 (1986) 163-171. 

D-2,3-Didehydro-erythro-hexono-1,4-lactone. See Erythorbic acid Didehydromenthane... 

CAS 89-65-6 EINECS/ELINCS 201-928-0 FEMA 2410 INS315 Synonyms Araboascorbic acid d-Araboascorbic acid D-2,3-Didehydro-erythro-hexono-1,4-lactone Erycorbin d-Erythorbic acid... 

Lactone D-Allono-1,4-lactone. z>-allo-Hexono-1,4-lactone... 

Lactone 6-Bromo-2,6-dideoxy-D-SLTahino-hexono-1,4-lactone [71672-01-0]... 

Lactone, tri-Ac 3,5,6-Tri-0-acetyl-2-deoxy-D-lyxo-hexono-1,4-lactone [69863-81-6]... 

Lactone, 2-Me 3-Deoxy-2-0-methyl-D-arabtxio-hexono-1,4-lactone [197296-31-4]... 

O -Me, 1,4-lactone 2,6-Dideoxy-3-0-methyl-D-nbo-hexono-1,4-lactone CtHuOa 160.169... 

Bromo-2,6-dideoxy-D-ara >wo -hexono-1,4-lactone, B-109 5-Bromo-2,5-dideoxy-D-//ireo -pentono-1,4-lactone, B-112 5-Bromo-2,5-dideoxy-D- i7/Aro -pentono-1,4-lactone, B-112... 

Deoxy-L-ara mo -hexono-1,4-lactone, T-34 3-Deoxy-D-rj6o -hexono-1,4-lactone, T-34 3-Deoxy-D-/yxo -hexono-1,4-lactone, T-34 3-Deoxy-L-r o -hexono-1,4-lactone, T-34 3-Deoxy-D-ara6mo -hexono-1,4-lactone, T-34 3-Deoxy-L-x> /o -hexono-1,4-lactone, T-34 2-Deoxy-D-ara6mo -hexono-1,4-lactone, D-187 2-Dtoxy-ribo -hexono-1,4-lactone, D-189... 

Deoxy-3,5,6-tri-O -methyl-D-ara6jno -hexono-1,4-lactone, D-187 2-Deoxy-3,4,6-tri-O -methyl-D-ara wo -hexono-1,5-lactone, D-187 6-Deoxy-2,3,4-tri- O -methyl-L-mannose, R-79... 

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