137792-57-5Relevant academic research and scientific papers
2-nitroglycal and efficient synthesis method thereof
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Paragraph 0059; 0061, (2021/08/06)
The invention discloses an efficient synthesis method of 2-nitroglycal, and belongs to the technical field of synthesis of sugar. The structure of the 2-nitroglycal is shown in the specification. Secondly, the invention also provides a preparation method of the 2-nitro saccharide alkene, and the preparation method provided by the invention can be used for efficiently preparing the 2-nitroglycal through one-step synthesis.
Tandem epoxidation-alcoholysis or epoxidation-hydrolysis of glycals catalyzed by titanium(IV) isopropoxide or Venturello's phosphotungstate complex
Levecque, Pieter,Gammon, David W.,Kinfe, Henok Hadgu,Jacobs, Pierre,De Vos, Dirk,Sels, Bert
supporting information; experimental part, p. 1557 - 1568 (2009/07/10)
Venturello's phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O 2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation-alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long-chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.
The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl3·DMF and (CF3SO2)2O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates
Lellouche,Koeller
, p. 693 - 696 (2007/10/03)
The two electrophilic Vilsmeier - Haack reagents POCl3·DMF 2 or (CF3SO2)2O·DMF 3 mediate the one-step and selective conversion of O-triethylsilyl (O-TES), O-tert-butyldimethylsilyl (O-TBDMS), O-tert-butyldiphenylsilyl (O-TBDPS), and O-triisopropylsilyl (O-TIPS) ethers of D-glucal to the corresponding C(6)-O-formates.
An expeditious route to Streptococci and Enterococci glycolipids via ring-opening of 1,2-anhydrosugars with protic acids
Timmers,Van Straten,Van Der Marel,Van Boom
, p. 471 - 487 (2007/10/03)
1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly β-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the β-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective α-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected α-diglucosyl glycerol derivative 25, which upon desilylation (→28), acylation (→29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.
A note on the solid-phase synthesis of oligosaccharides by the Danishefski approach
Timmers, C. M.,Marel, G. A. van der,Boom, J. H. van
, p. 609 - 610 (2007/10/02)
The ZnCl2-mediated glycosidation of an α-1,2-epoxide, prepared by epoxidation of a glycal with 3,3-dimethyldioxirane, with an incoming glycal acceptor is not a priori, as advocated by Danishefski et al., a stereospecific process.
Radical Cyclization Routes to Bridged Pyranosides as Precursors of Densely Functionalized Cycloalkanes
Alonso, R. A.,Vite, G. D.,McDevitt, R. E.,Fraser-Reid, B.
, p. 573 - 584 (2007/10/02)
Glycals derived from hexapyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group.Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on
