Journal ArticleDOI
Vilsmeier-haack reactoin of glycals-a short route to C-2-formyl glycals☆
TLDR
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.read more
Citations
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Journal ArticleDOI
Synthesis of Substituted 1‐\C\‐Phenyl‐D‐Tetritols and 1‐C‐(1H‐Pyrazol‐4‐yl)‐D‐tetritols by Ring Transformation of 2‐Formylglycals
TL;DR: Zschunke et al. as discussed by the authors used dialkyl 3 −oxoglutarates in the presence of base to furnish the 5 −[(1R,2R(S),3R)•1,2,4•tris(benzyloxy)•3−hydroxy‐butyl]•2•hydroxy−isophthalic acid dialkyls esters 2a−d.
Journal ArticleDOI
Trifluoroacetic acid-mediated facile transformation of 2-C-hydroxymethyl-D-glycals to chiral pyrano[2,3-b]benzopyrans.
TL;DR: Treatment of 2-C-hydroxymethyl-D-glycals with phenols in trifluoroacetic acid at ambient temperature leads to an extremely facile transformation affording chiral pyrano[2,3-b]benzopyrans in high yields.
Book ChapterDOI
Formation and Reactions of Glycal Derivatives
TL;DR: In this paper, the generic name "glycals" was adopted for this class of unsaturated sugars, which are in fact extensively substituted cyclic vinyl ethers and are also encountered as structural motifs in the total syntheses of some complex natural products.
Journal ArticleDOI
Use of XtalFluor-E as an Alternative to POCl3 in the Vilsmeier-Haack Formylation of C-2-Glycals.
TL;DR: XtalFluor-E ([Et2NSF2]BF4) is reported as an alternative to POCl3 in the Vilsmeier-Haack formylation reaction of C-2-glycals and its use was extended to the synthesis of a C- 2 -formylated disaccharide glycal.
Journal ArticleDOI
Pyrimidine acyclo-C-nucleosides by ring transformations of 2-formyl-L-arabinal.
TL;DR: The protected 2-formyl-L-arabinal 2 reacted with thiourea and cyanamide in the presence of sodium hydride to afford via ring transformations the 5-[1R,2S-1,2-bis(benzyloxy)-3-hydroxypropyl]-1, 2-dihydropyrimidines 3 and 4, respectively.
References
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Journal ArticleDOI
C-glycoside synthesis by palladium-mediated glycal-aglycon coupling reactions
Journal ArticleDOI
Die Konstitution der Lycotetraose
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
Journal ArticleDOI
Studies on unsaturated sugars with particular reference to the synthesis of 6-Deoxy-6-fluoro derivatives
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.
Journal ArticleDOI
The preparation of C-arylglycals. The palladium-catalyzed coupling of 3,4,6-tri-O-(tert-butyldimethylsilyl)-1-(tributylstannyl)-D-glucal and aryl bromides
Richard Friesen,Claudio Sturino +1 more
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.
Journal ArticleDOI
A Rapid Route to Hex-1-enopyran-3-uloses
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.
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A new ferrier system: 2-C-acetoxymethylglycals. A covenient entry to 2-C-methylene glycosides
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