58871-09-3Relevant academic research and scientific papers
MOLECULAR PROBES FOR ANALYSIS OF METABOLISM OF GLYCOLYSIS INHIBITORS PRODRUGS AND SYNTHESIS METHODS THEREFORE
-
Page/Page column 8-9, (2020/03/05)
The present invention relates to compounds according to structure (I) whereby one of R1 to R3 is -OCOCD3 and the other two are either hydroxyl or OAc, their synthesis and their use in for the analysis of the metabolism of glycolysis inhibitors.
Using DMF as Both a Catalyst and Cosolvent for the Regioselective Silylation of Polyols and Diols
Lv, Jian,Luo, Tao,Zou, Dapeng,Dong, Hai
, p. 6383 - 6395 (2019/11/05)
Highly regioselective silylation of primary hydroxyl groups of unprotected polyols and diols was obtained by the use of a mixed solvent of MeCN/DMF (10:1) in this study. DMF was discovered to be a good catalyst in this reaction, although the silylation us
NOVEL ACETATES OF 2-DEOXY MONOSACCHARIDES WITH ANTICANCER ACTIVITY
-
Paragraph 0096; 0098; 0099, (2017/04/01)
Novel compounds and methods of using the same to inhibit glycolysis and treat cancer and other diseases are provided herein.
Total synthesis of (-)-isatisine A via a biomimetic benzilic acid rearrangement
Xiao, Mingxing,Wu, Wei,Wei, Lin,Jin, Xiaojie,Yao, Xiaojun,Xie, Zhixiang
, p. 3705 - 3714 (2015/05/20)
The biomimetic total synthesis of potential anti-HIV (-)-isatisine A, a novel alkaloid with an unprecedented fused tetracyclic skeleton, was accomplished in eight steps from indole and known 4,6-O-isopropylidene-protected glucal. The synthetic strategy was inspired primarily by the proposed biogenetic hypothesis that indole C-furanoside would be derived from indole C-glucoside via a ring contractive benzilic acid rearrangement. The biogenetic hypothesis was enabled by model studies: the O-glucoside was converted to O-furanoside via a benzilic acid rearrangement.
Total synthesis of cryptopyranmoscatone B1 from 3,4,6-tri-O-acetyl-d-glucal
Sabitha, Gowravaram,Reddy, S. Siva Sankara,Yadav
supporting information; experimental part, p. 6259 - 6261 (2011/01/04)
The first stereoselective total synthesis of the natural cryptopyranmoscatone B1 has been accomplished from 3,4,6-tri-O-acetyl-d-glucal. In addition to the double cross-metathesis reaction, a tandem nucleophilic addition-diastereoselective reduction of an
Stereocontrolled intramolecular aziridination of glycate: Ready access to aminoglycosides and mechanistic insights from DFT studies
Lorpitthaya, Rujee,Xie, Zhi-Zhong,Kuo, Jer-Lai,Liu, Xue-Wei
scheme or table, p. 1561 - 1570 (2009/04/06)
Stereocontrolled intramolecular aziridination of the glycal-derived sulfamates offers a highly efficient strategy to divergently prepare aminoglycosides. Rhodium-catalyzed nitrogen-atom transfer to C=C bonds formed semistable aziridines, which were subjected to various nucleophiles (C, O, S, and N) to give cyclic sulfamate-containing aminosugar derivatives selectively. The second nucleophilic displacement of sulfonyloxy moieties of [1,2,3]-oxathiazepane-2,2-dioxides allows straightforward access to aminoglycosides with selective α- or β-linkages. This approach is operationally simple, complements existing methods, and is a versatile protocol for the synthesis of polyfunctionalized amino sugars. In addition, the mechanism of the rhodium-catalyzed intramolecular aziridination of glycals and its ring-opening reaction was extensively studied by using DFT calculations.
Adducts of uridine and glycals as potential substrates for glycosyltransferases
Wandzik, Ilona,Bieg, Tadeusz
, p. 401 - 416 (2008/03/13)
We report on the synthesis of 2-deoxyglycosyl derivatives of uridine as potential donor substrates for glycosyltransferases. The totally stereoselective synthesis is accomplished by two sequential addition reactions of uridine derivatives to glycals promo
Cesium carbonate-promoted Michael-type addition of thiols to hex-1-en-3-ulose: A practical synthesis of 2-deoxy-1-thio-α-hexopyranosid- 3-ulose template
Ganguly, Debashis,Tang, Haiqun,Rodriguez, Michael J.
, p. 4219 - 4226 (2008/03/13)
The template 2-deoxy-1-thio-α-hexopyranosid-3-ulose was synthesized in quantitative yield and high diastereoselectivity by 1,4-addition of aryl and alkyl thiols to hex-1-en-3-ulose promoted by cesium carbonate in THF. Copyright Taylor & Francis Group, LLC
Synthesis of a-ring synthon of 19-nor-1alpha,25-dihydroxyvitamin D3 from (D)-glucose
-
Page 4, (2010/02/07)
The present invention provides a method for the synthesis of an A-ring synthon phosphine oxide used in the preparation of 19-nor vitamin D compounds, and to novel synthetic intermediates formed during the synthesis. The new method prepares the phosphine oxide from (D)-glucose.
Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides
Aurrecoechea, José M.,Gil, Jesús H.,López, Beatriz
, p. 7111 - 7121 (2007/10/03)
The effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne did not afford the expected product. The presence of peripheral alkoxy substituents leads to variable stereoselectivities that depend on the number and orientation of such groups. Thus, an isolated OBn substituent at C(3) (carbohydrate numbering) exerts a significant stereochemical control while additional substitution with the same group at C(4) either enhances or drastically reduces stereoselectivity depending on its orientation (α or β, respectively).
