2,3-O-ISOPROPYLIDENE-L-ERYTHROTETRURONIC ACID AND -L-ERYTHROSE, AND THE METHYL D-ERYTHRO- AND D-THREO-TETROFURANOSIDES

doi:10.1139/V60-299

Paper

2,3-O-ISOPROPYLIDENE-L-ERYTHROTETRURONIC ACID AND -L-ERYTHROSE, AND THE METHYL D-ERYTHRO- AND D-THREO-TETROFURANOSIDES

Published Nov 1, 1960 · J. Baxter, A. Perlin

Canadian Journal of Chemistry

Q3 SJR score

30

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0

Influential Citations

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Abstract

Oxidation of 2,3-O-isopropylidene-β-L-rhamnose (I) with hypoiodite, followed by periodate cleavage of the derived aldonic acid, affords 2,3-O-isopropylidene-L-erythrotetruronic acid. Reduction of I with sodium borohydride and periodate oxidation of the resulting glycitol gives 2,3-O-isopropylidene-L-erythrose. Both products have been obtained in high yield, and are readily hydrolyzed to L-erythrotetruronic acid and L-erythrose, respectively.Methyl α- and β-D-erythro- and D-threo-tetrofuranosides have been prepared by the Fischer glycoside synthesis from D-erythrose- and D-threose-formates, respectively. A notable anomeric difference in the lead tetraacetate oxidation behavior of the methyl D-threosides has been observed, the β-anomer being more reactive than the α-anomer.

Study Snapshot

This study demonstrates the high yield and ease of preparation of 2,3-O-isopropylidene-L-erythrotetruronic acid and -L-erythrose, as well as methyl D-erythro- and D-threo-tetrofuranosides, with the

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

2,3-O-ISOPROPYLIDENE-L-ERYTHROTETRURONIC ACID AND -L-ERYTHROSE, AND THE METHYL D-ERYTHRO- AND D-THREO-TETROFURANOSIDES

References

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Gas-liquid partition chromatography effectively separates various carbohydrate derivatives, enabling accurate quantification of components in mixtures.

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This new method for preparing D-erythrose and L-glyceraldehyde yields at least 80% of theory and allows for easy intermolecular association among sugars.

Aspects of stereochemistry—I : Properties and reactions of some diols

Intramolecular hydrogen-bonding in certain diols can affect their stabilities and reaction rates, with ring oxygen presence influencing their zone electrophoretic mobility in alkaline borate buffers.

Citations

Synthese Des 5-Desoxy-5,5,5-Trifluoro-d- et -l-Pentofuranoses

5-deoxy-5,5,5-trifluoropentofuranoses can be synthesized using various methods, enabling the production of various derivatives of ribose, lyxose, and arabinose.

Clay Catalyzed Acetonation:A Simple Method for the Preparation of Isopropylidene Carbohydrates

Clay-catalyzed acetonation is a simple method for preparing isopropylidene carbohydrates from various monosaccharides and ribonucleosides in good yields under mild reaction conditions.

Stéréosélectivité comparée de la réduction de trifluorométhylcétones et des méthylcétones correspondantes: nouvelles voies d'accès à des dérivés trifluorométhylés de pentoses

Selectivity in reducing trifluoroacetyl-1,3-dioxanes and 1,3-dioxolanes with DIBAH or L-Selectride leads to the synthesis of 5,5,5-trifluorinated derivatives of D and L-pento

D‐Erythronolactone and 2,3‐O‐Isopropylidene‐L‐erythrose as C4 Building Units: An Efficient Synthesis of both Enantiomers of endo‐Brevicomin and its 7‐Vinyl Analogues

This study demonstrates an efficient synthesis of both enantiomers of endo-brevicomin and its 7-vinyl analogues from D-erythronolactone and 2,3-O-isopropylidene-L-erythrose, yielding key compounds 5a and

Trifluoromethylation of sugar 1,4-lactones : Synthesis of 5-deoxy-5,5,5-trifluoro-D and L-ribose and lyxose derivatives

Trifluoromethylation of sugar 1,4-lactones allows for the synthesis of 5-deoxy-5,5,5-trifluoro-D, L-ribose, and lyxose derivatives with 30-40% overall yield.

An acyl radical initiated tandem 7-endo/5-exo radical cyclization approach to enantiomerically pure bicyclo[5.3.0]decan-2-ones

This study presents a tandem radical cyclization approach for enantiomerically pure bicyclo[5.3.0]decan-2-ones, using erythro and threo 4,5-dihydroxyhept-6-enoic acids and phenylseleno esters.

Synthesis of L-(4-2H) erythrose, L-(1-13C, 5-2H) arabinose and L-(2-13C, 5-2H) arabinose and identification of the intermediates by 2H and 13C-N.M.R. spectroscopy

This study demonstrates that L-(1-13C, 5- 2 H)arabinose and L-(2- 13C, 5- 2 H)arabinose can be synthesized by degrading 2,3-O-isopropylidene--l-rhamnofuranose, with only one