2873-29-2Relevant articles and documents
A new catalyst for the reductive elimination of acylated glycosyl bromides to form glycals
Stick, Robert V.,Stubbs, Keith A.,Tilbrook, D. Matthew G.,Watts, Andrew G.
, p. 83 - 85 (2002)
Ethylene-N,N′-bis(salicylideneiminato(IV)) {VO(salen)} was developed as a catalyst for the reductive elimination of acylated glycosyl bromides to form glycals. VO(salen) to be an effective catalyst for the preparation of glycals on a multi-gram scale. The catalyst was green in colour and changed to brown as the reaction progress.
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Takiura,K.,Honda,S.
, p. 369 - 377 (1972)
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A convenient synthesis of glycals employing in-situ generated Cp2TiCl
Hansen, Thomas,Krintel, Sussie L.,Daasbjerg, Kim,Skrydstrup, Troels
, p. 6087 - 6090 (1999)
Reductive elimination of acetylated glycosyl bromides to the corresponding glycal is easily achieved by mixing the bromide with Cp2TiCl2 and Mn in THF, and hence does not require the separate preparation of Cp2TiCl using glove-box techniques.
Long-lived glycosyl-chromium(III) complex intermediates in aqueous medium. Preparation of pyranoid glycals
Kovacs, Gyoengyver,Gyarmati, Julianna,Somsak, Laszlo,Micskei, Karoly
, p. 1293 - 1296 (1996)
Acetylated glycosyl-chromium(III)L (L=EDTA, NTA, IDA) complex intermediates (1) were detected in aqueous medium, with half-life-times of 30-300 minutes. The decay of these intermediates led to glycals (7-9) of high purity in preparatively usable 70-90% yields.
Titanium(III) reagents in carbohydrate chemistry: Glycal and C-glycoside synthesis
Spencer, Roxanne P.,Schwartz, Jeffrey
, p. 2103 - 2112 (2000)
Titanocene(III) chloride and zirconcene(III) chloride are effective and mild reagents for radical generation in organic synthesis. In carbohydrate chemistry, these species are useful for the conversion of glycosyl halides to glycals, and for the stereospecific preparation of C-glycosides. In all cases, the 1-glycosyl radical is an active intermediate, generated by reaction of carbohydrate substrates with the organometallic. (C) 2000 Elsevier Science Ltd.
Method for efficiently constructing 1, 2-cis-2-nitro-glucoside and galactoside
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Paragraph 0038; 0062, (2021/08/11)
The invention discloses a method for efficiently constructing 1, 2-cis-2-nitro-glucoside and 1, 2-cis-2-nitro-galactoside, and belongs to the technical field of organic synthesis. According to the preparation method, the 1, 2-cis-2-nitro-glucoside and the 1, 2-cis-2-nitro-galactoside can be efficiently prepared through one-step synthesis. According to the present invention, the organic catalysis stereoselective glycosylation method is successfully applied to the sugar chemical total synthesis so that the problem of the construction of the 1, 2-cis-glucosidic bond between the most key sugar units is solved, and the foundation is established for the completion of the subsequent poly O-antigen total synthesis. The work has important reference value for related immunological research and vaccine development in the future.
Preparation method of 3, 4, 6-O-triacetyl-D-glucal
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Paragraph 0012-0014, (2020/05/14)
The invention relates to a preparation method of Tri-O-acetyl-D-glucal, which mainly solves the problems of volatile reagent, irritant smell, high cost and the like in the existing method. The technical scheme of the invention is as follows: the preparation method of 3, 4, 6-O-triacetyl-D-glucal comprises the following steps: peracetylated D-glucose is prepared by catalyzing D-glucose in glacial acetic acid with strong acid; the peracetylated D-glucose is brominated by a glacial acetic acid solution of hydrogen bromide to obtain brominated peracetylated D-glucose; and the brominated peracetylated D-glucose is reduced by zinc powder in an ammonium chloride solution to obtain a final product 3, 4, 6-O-triacetyl-D-glucal. The product provided by the invention has important application in thefields of glycopeptides and other polypeptide drugs.
Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects
St-Gelais, Jacob,C?té, émilie,Lainé, Danny,Johnson, Paul A.,Giguère, Denis
supporting information, p. 13499 - 13506 (2020/10/02)
In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.