18. Ascorbic acid and synthetic analogues

Baird, D. K.; Haworth, Walter Norman; Herbert, R. W.; Hirst, E. L.; Smith, F.; Stacey, M.

doi:10.1039/jr9340000062

Cited by 25 publications

(8 citation statements)

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“…First order analysis indicated coupling constants, J1,2 = 2.0, J2,3 = 3.1, J 3 , 4 = 3.0, and J4,5 = 9.2 c.p.s., which are compatible with the structure and conformation indicated in 6 (48,49). The occurrence of appreciable (about 20%) oxide ring-opening to diequatorial product (9) in this reaction is readily understood since the metboxy group must be expected to destabilize the transition state leading to the diaxial product by non-bonded interaction with the entering iodide ion. The reactions of the other epoxides all proceeded to diaxial product Can.…”

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confidence: 60%

“…The p-D-gl~tco configuration was required for the higher melting (m.p. 230") isomer (9) in view of the coupling interactions observed in the n.m.r. spectrum of its 0-acetyl derivative.…”

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confidence: 99%

“…The antibiotic cordycepin (3,4) is formed from adenosine (5) probably via 2',3'-dehydrodeoxyadenosine (6). Unsaturated compounds of this type occur naturally, for example, ascorbic acid (7)(8)(9)) and a nucleoside antibiotic blasticidin S (6,10).…”

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confidence: 99%

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Preparation of unsaturated carbohydrates. A facile synthesis of methyl 4,6-O-Benzylidene-D-hex-2-enopyranosides

Lemieux¹,

Fraga²,

Watanabe³

1968

Can. J. Chem.

104

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A simple method was explored for the preparation of methyl 4,6-0-benzylidene-hex-2-enopyranosicles. Methyl 2,3-anhydro-4,6-0-benzylidene-D-hexopyranosides were converted to diaxial iodohydrins using sodium iodide in acetone which contained sodium acetate and acetic acid. Trcatment of the iodohydrins with either methane-or p-toluenesulfonyl chloride in refluxing pyridine yielded the 2,3-unsaturated derivative in excellent yield. The four isomers for methyl 4,6-0-benzylidene-D-hex-2-enopyranoside were thus prepared. The rotations of the anomeric pairs followed Hudson's rules of isorotation. Evidence is provided that, in the absence of strong destabilizing interactions in the product, the epoxide ring of one of the above-mentioned 2,3-anhydroglycosides is opened by lithium iodide in ether to form the iodohydrin as the lithium alkoxide in high yield. This observation provides an explanation for the reduction of methyl 2,3-anhydro-4,6-0-benzylidene-a-D-allopyranoside to 4,6-0-benzylidene-D-allal. Reaction of methyl 4,6-0-benzylidene-2-deoxy-2-iodo-~-~-idopyranoside with methyl lithium provided 4,6-0-benzylidene-D-gulal. The conformational properties of a number of the compounds prepared and of acetylated methyl pentopyranosides, as derived from their nuclear magnetic resonance parameters, are discussed with particular reference to the role that geminal coupling constants may play in the determination of configuration and conformational equilibria.

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confidence: 60%

“…The p-D-gl~tco configuration was required for the higher melting (m.p. 230") isomer (9) in view of the coupling interactions observed in the n.m.r. spectrum of its 0-acetyl derivative.…”

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confidence: 99%

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Preparation of unsaturated carbohydrates. A facile synthesis of methyl 4,6-O-Benzylidene-D-hex-2-enopyranosides

Lemieux¹,

Fraga²,

Watanabe³

1968

Can. J. Chem.

104

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“…d-Gluco-ascorbic acid (d-3-ketoglucoheptonofuranolactone) [Ault et al, 1933] and d-galacto-ascorbic acid [Baird et al, 1934] were found to be totally inactive in daily doses of 10 mg. (Zilva, unpublished results).…”

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confidence: 99%

The behaviour of l-ascorbic acid and chemically related compounds in the animal body. Antiscorbutic activity in relation to retention by the organism

Zilva

1935

Biochemical Journal

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ALTHOUGH 1-ascorbic acid (I-xylo-ascorbic acid) is the most active antiscorbutic substance so far known, other chemically related compounds have been shown to possess antiscorbutic activity. Of these d-arabo-ascorbic acid (d-erythro-3-ketohexonic acid lactone) [Maurer and Schiedt, 1933] possesses about 1/20 [Dalmer and Moll, 1933;Demole, 1934], 1-rhamno-ascorbic acid (6-methyl-1-arabo-3-ketohexonic acid lactone) 1/5 [Reichstein et al., 1935] of the activity of i-ascorbic acid. A homologue i-gluco-ascorbic acid is 1/40 active [Reichstein, 1934 and private communication]. This compound was tested recently by the writer and, as will be seen from with the activity claimed for it. Unfortunately, owing to scarcity of material, a more accurate assessment was not carried out.In contradistinction to the above compounds d-ascorbic acid failed to show antiscorbutic activity when administered to guinea-pigs on a scorbutic diet in daily doses of 20 mg. [Demole, 1934]. d-Gluco-ascorbic acid (d-3-ketoglucoheptonofuranolactone) [Ault et al., 1933] and d-galacto-ascorbic acid (d-3-ketogalIactoheptonofuranolactone) [Baird et al., 1934] were found to be totally inactive in daily doses of 10 mg. (Zilva, unpublished results).

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“…Since oc-ethyltetronic acid (I, R1 = Et; R2 = H) and a-acetyltetronic acid (II, R1= CH3; R2 = H) occupy special positions as reference substances in connection with the subject matter of this paper their absorption spectra will be R1 [Herbert et al, 1933;Baird et at., 1934]. Reference to the formulae shows a close structural similarity between the two substances and ascorbic acid is in fact an example of formula I with R1= OH and R2=-CHOH.CH2OH.…”

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Absorption spectra of the metabolic acids of Penicillium Charlesii and their relationship to the absorption spectrum of ascorbic acid

Herbert

Hirst

1935

Biochemical Journal

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18. Ascorbic acid and synthetic analogues

Cited by 25 publications

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Preparation of unsaturated carbohydrates. A facile synthesis of methyl 4,6-O-Benzylidene-D-hex-2-enopyranosides

Preparation of unsaturated carbohydrates. A facile synthesis of methyl 4,6-O-Benzylidene-D-hex-2-enopyranosides

The behaviour of l-ascorbic acid and chemically related compounds in the animal body. Antiscorbutic activity in relation to retention by the organism

Absorption spectra of the metabolic acids of Penicillium Charlesii and their relationship to the absorption spectrum of ascorbic acid

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