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Journal ArticleDOI

Vilsmeier-haack reactoin of glycals-a short route to C-2-formyl glycals☆

29 Jul 1991-Tetrahedron Letters (Pergamon)-Vol. 32, Iss: 31, pp 3875-3878
TL;DR: A short and straightforward route has been accomplished for the synthesis of C-2-formyl glycals by a Vilsmeier-Haack reaction of glycals.
About: This article is published in Tetrahedron Letters.The article was published on 1991-07-29. It has received 52 citations till now. The article focuses on the topics: Glycal.
Citations
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Journal ArticleDOI
TL;DR: Reaction of 2-C-hydroxymethyl-d-galactal with 2,6-dimethylphenol in the presence of montmorillonite K-10 led to a novel domino transformation affording 4-(5',6'-dihydro-4H-pyran-3'-ylmethyl)-2, 6-dimmethylphenol, which led to totally unexpected transformations.

12 citations

Journal ArticleDOI
TL;DR: Lichtenthaler et al. as mentioned in this paper showed that 2-formylgalactal 1, presented as an unsaturated sugar derivative with push-pull functionalization, with guanidinium and amidinium salts, with basic conditions to furnish the substituted 5-(1,2,4-tri-O-benzyl-d-lyxo-1, 2,3, 4-tetrahydroxybutyl)benzo[4,5]imidazo[ 1,2-a]pyrimidine (5) and

11 citations


Cites background or methods from "Vilsmeier-haack reactoin of glycals..."

  • ...This mixture was then dropwise added to another stirred solution of 1([15]) (100 mg, 0....

    [...]

  • ...Starting from D-galactose it is possible to synthesize the respective 2-formylglycal in six reaction steps.([15]) As we described in previous papers, – 14] this C-branched, unsaturated sugar with push-pull activation allowed displacement and ring transformation reactions with C- or N-nucleophiles....

    [...]

Journal ArticleDOI
TL;DR: A new and efficient method for the facile synthesis of C-2 branched carbohydrates has been developed using an intramolecular radical cyclization fragmentation reaction and an unexpected furanoside was obtained from a tributyltin iodide-promoted rearrangement of the radical intermediate.

11 citations

Journal ArticleDOI
TL;DR: In this article, a 2-vinyl glucal derivative was synthesized by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal.

10 citations

Journal ArticleDOI
TL;DR: A convenient two-step strategy is reported for the synthesis of fluorinated optically pure acyclo-C-nucleoside analogues starting from simple glycals containing a carbohydrate side chain linked to the heterocyclic ring.

9 citations

References
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Journal ArticleDOI
TL;DR: The Tetrasaccharid Lycotetraose, das im Tomatin with Tomatidin verknupft ist, lies sich strukturell aufklaren, indem 1. Tomatin, 2. Glykosid (β 1-Tomatin) and 3. das xylosefreie Trisaccharide Triscarid (Lycotriose), letzteres nach katalytischer Hydrierung zum Lycotriit, with Methyljodid and Silber
Abstract: Das Tetrasaccharid Lycotetraose, das im Tomatin mit Tomatidin verknupft ist, lies sich strukturell aufklaren, indem 1. Tomatin, 2. das daraus durch Abspaltung von D-Xylose gewonnene Glykosid (β1-Tomatin) und 3. das xylosefreie Trisaccharid (Lycotriose), letzteres nach katalytischer Hydrierung zum Lycotriit, mit Methyljodid und Silberoxyd in Dimethylformamid permethyliert wurden. Aus den Spaltstucken der permethylierten Verbindungen, die kristallisiert erhalten wurden, ergibt sich fur die Lycotetraose die verzweigte Konstitution einer β-D-Glucopyranosyl(1 2Glucose)-β-D-xylopyranosyl(1 3Glucose)-β-D-glucopyranosyl(1 4Galaktose)-α-D-galaktopyranose und damit fur das Tomatin die Formel I. Auch aus Demissin last sich, unter Abspaltung von D-Xylose und des Aglykons, kristallisierte Lycotriose gewinnen.

110 citations

Journal ArticleDOI
TL;DR: Three fluoro-substituted unsaturated sugars have been synthesized by transformations within the D-glucal and ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside series.
Abstract: Three fluoro-substituted unsaturated sugars have been synthesized by transformations within the D-glucal and ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside series. A number of the intermediate unsaturated sugars not previously described have been characterized. The advantages of the t-butyldimethylsilyl blocking group in such syntheses are described.

71 citations

Journal ArticleDOI
TL;DR: The palladium-catalyzed couplings of the protected 1-(tributylstannyl)-D-glucal 1 and substituted aryl bromides provide the corresponding C-arylglucals and a dimer as mentioned in this paper.
Abstract: The palladium-catalyzed couplings of the protected 1-(tributylstannyl)-D-glucal 1 and substituted aryl bromides provide the corresponding C-arylglucals and a dimer

70 citations

Journal ArticleDOI
TL;DR: In this article, it was shown that triacetyl glucal can be converted to 6-O-triphenylmethyl ether or 6 O-benzoyl ester to promote solubility in chloroform, and the derivatives are oxidized in that solvent in 12 h or less.
Abstract: Whereas the pseudo-axial 3-hydroxyl group of allal derivatives is known to be inert to manganese dioxide oxidation, the equatorial counterpart in glucal derivatives is shown to be readily oxidized. Thus glucal is converted to the 6-O-triphenylmethyl ether or 6-O-benzoyl ester to promote solubility in chloroform, and the derivatives are oxidized in that solvent in 12 h or less.Acetonation of glucal is readily accomplished in 45 min using 2,2-dimethoxypropane and p-toluenesulfonic acid in dimethylformamide; the product may be oxidized directly either with manganese dioxide or dipyridine chromium oxide. Thus it is possible to obtain 1–3-g quantities of the crystalline acetonated enone from triacetyl glucal (via deacetylation, acetonation, and oxidation) in 3–4 h.If the acetonation medium stands for 2 h methyl 2,3-dideoxy-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside is obtained. The mechanism of its formation in the reaction medium is discussed.

64 citations