53657-42-4Relevant articles and documents
Synthesis of 3-deoxyaldulosonic acid esters by one-carbone chain extension of glycal-derived lactone precursors
Horton,Issa,Priebe,Sznaidman
, p. 105 - 118 (1993)
A convenient preparative route is described for 3-deoxyaldulosonic acids. Glycal precursors are oxidatively converted into 2-deoxyaldonolactones, which react with 1,3-dithian-2-yl anion to afford 1,3-propanediyl dithioacetals of higher 3-deoxyaldosuloses. Deprotection with mercuric salts in wet or dry alcohols gave high yields of the corresponding alkyl aldulosonates. Preparative reaction conditions were optimized and the anomeric configurations of the ketopyranose products were established by 13C NMR. A convenient preparative route is described for 3-deoxyaldulosonic acids. Glycal precursors are oxidatively converted into 2-deoxyaldonolactones, which react with 1,3-dithian-2-yl anion to afford 1,3-propanediyl dithioacetals of higher 3-deoxyaldosuloses. Deprotection with mercuric salts in wet or dry alcohols gave high yields of the corresponding alkyl aldulosonates. Preparative reaction conditions were optimized and the anomeric configurations of the ketopyranose products were established by13C NMR.
Extended RCM-ROM sequences: a novel approach to polyunsaturated trisaccharides
Donnard, Morgan,Tschamber, Théophile,Eustache, Jacques
, p. 7325 - 7327 (2008)
The first examples of RCM-ROM-RCM-ROM-RCM sequences involving non-strained heterocyclic relays are described. The method can be used for the preparation of polyunsaturated trisaccharides.
Isolation, Structure, and Total Synthesis of the Marine Macrolide Mangrolide D
Gong, Junyu,Li, Wei,Fu, Peng,Macmillan, John,De Brabander, Jef K.
, p. 2957 - 2961 (2019)
The isolation, characterization, and total synthesis of the macrocyclic polyene mangrolide D is reported. A 16-step total synthesis relies on robust Suzuki and ring-closing metathesis reactions, and an iron-catalyzed hydroazidation of an exomethylene subs
Synthesis of the α-Linked Digitoxose Trisaccharide Fragment of Kijanimicin: An Unexpected Application of Glycosyl Sulfonates
Bennett, Clay S.,Mizia, J. Colin,Syed, Mohammed U.
supporting information, p. 731 - 735 (2022/01/28)
Previously, we demonstrated that glycosyl tosylates are effective for the synthesis of β-glycosides of gluco-configured 2-deoxy sugars. Here, we show the same sulfonate system can be used for the selective synthesis of α-glycosides containing the allo-con
Me3SI-promoted chemoselective deacetylation: a general and mild protocol
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj
, p. 19310 - 19315 (2021/06/03)
A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.
Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals
Bennett, Clay S.,Nguyen, Tu-Anh V.,Pohl, Nicola L. B.,Yalamanchili, Subbarao
supporting information, p. 3254 - 3257 (2020/05/14)
An efficient, modular continuous flow process towards accessing two orthogonally protected glycals is described with the development of reaction conditions for several common protecting group additions in flow, including the addition of benzyl, naphthylme