137893-35-7Relevant academic research and scientific papers
An Unexpected Sialylation: Total Syntheses of GM4 and a Positional Isomer
Gervay, Jacquelyn,Peterson, John M.,Oriyama, Takeshi,Danishefsky, Samuel J.
, p. 5465 - 5468 (1993)
The use of glycals 3 and 4 as precursors to 1,2-ahhydrosugars greatly simplifies the installation of a β-linked ceramide glycoside.By permuting the introduction of the ceramide and the sialic acid, one can access the ganglioside GM4 (1) and, by an unexpected regioselective glycosylation, its NeuAc (2->2) Gal positional isomer 10.
2-nitroglycal and efficient synthesis method thereof
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Paragraph 0063-0064, (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.
Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides
Li, Zhongjun,Meng, Shuai,Yao, Wang,Zhong, Wenhe
supporting information, (2020/04/09)
A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.
Method for stereoselectively synthesizing beta-2-deoxyglycoside bond
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Paragraph 0031-0032; 0038, (2019/07/04)
The invention discloses a method for stereoselectively synthesizing a beta-2-deoxyglycoside bond. The method comprises the following steps: performing glycosylation on 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene serving as a donor, a saccharide receptor and a molecular sieve under the condition of the existence of an accelerant, wherein an isopropyl acetal protectivegroup is mounted on a 3-site hydroxyl and a 4-site hydroxyl of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene and a TBDPS is mounted on the 6-site of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene; through the synergistic effect of the protective groups, sugar ring conformation of the donor is controlled, and the stereoselective synthesis of a beta-configuration is realized. According to the method, the stereoselectivity of the glycosylation can be controlled effectively and stereoselectively; the method is wide in substrate application range and convenient to operate; raw materials are easy to obtain; side reactions of the glycosylation are few; a target product is high in yield and optical purity; a new design thought is provided for the research of the glycosylation.
General Strategy for Stereoselective Synthesis of β- N-Glycosyl Sulfonamides via Palladium-Catalyzed Glycosylation
Dai, Yuanwei,Zheng, Jianfeng,Zhang, Qiang
supporting information, p. 3923 - 3927 (2018/07/21)
A highly efficient and mild glycosylation reaction between 3,4-O-carbonate glycal and N-tosyl functionalized aliphatic and aromatic amines via palladium-catalyzed decarboxylative allylation is disclosed. A wide range of highly functionalized 2,3-unsaturat
Syntheses of α- and β-glycosyl donors with a disaccharide β-D-Gal-(1→3)-D-GalNAc backbone
Cheshev,Kononov,Tsvetkov,Shashkov,Nifantiev
, p. 419 - 429 (2007/10/03)
The synthesis of thioglycoside glycosyl donors with a disaccharide β-D-Gal-(1 → 3)-D-GalNAc backbone was studied using the glycosylation of a series of suitably protected 3-monohydroxy- and 3,4-dihydroxyderivatives of phenyl 2-azido-2-deoxy-1-thio-α- and 1-thio-β -D-galactopyranosides by galactosyl bromide, fluoride, and trichloroacetimidate. In the reaction with the monohydroxylated glycosyl acceptor, the process of intermolecular transfer of thiophenyl group from the glycosyl acceptor onto the cation formed from the molecule of glycosyl donor dominated. When glycosylating 3,4-diol under the same conditions, the product of the thiophenyl group transfer dominated or the undesired (1 → 4), rather than (1 → 3)-linked, disaccharide product formed. The aglycon transfer was excluded when 4-nitrophenylthio group was substituted for phenylthio group in the galactosyl acceptor molecule. This led to the target disaccharide, 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β -D-galactopyranosyl)-1-thio-β-D-galactopyranoside, in 57% yield. This disaccharide product bears nonparticipating azido group in position 2 of galactosamine and can hence be used to form α-glycoside bond. Azido group and the aglycon nitro group were simultaneously reduced in this product and then trichloroacetylated, which led to the β-glycosyl donor, 4-trichloroacetamidophenyl 4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) -1-thio-2-trichloroace-tamido-β-D-galactopyranoside, in 62% yield. The resulting glycosyl donor was used in the synthesis of tetrasaccharide asialo-GM1.
Application of glycals to the synthesis of oligosaccharides: Convergent total syntheses of the Lewis X trisaccharide sialyl Lewis X antigenic determinant and higher congeners
Danishefsky, Samuel J.,Gervay, Jacquelyn,Peterson, John M.,McDonald, Frank E.,Koseki, Koshi,Griffith, David A.,Oriyama, Takeshi,Marsden, Stephen P.
, p. 1940 - 1953 (2007/10/02)
Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLex tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The us
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
SELECTIVE CLEAVAGE OF t-BUTYLDIPHENYLSILYL ETHERS IN THE PRESENCE OF t-BUTYLDIMETHYLSILYL ETHERS
Shekhani, Mohammed Saleh,Khan, Khalid Mohammed,Mahmood, Khalid,Shah, Pir Mozzam,Malik, Sohail
, p. 1669 - 1670 (2007/10/02)
The rate of cleavage of t-butyldiphenylsilyl (TBDPS) ethers with sodium hydride in hexamethylphosphoric triamide (HMPA) is significantly faster than that of the corresponding t-butyldimethylsilyl (TBDMS) ethers.The TBDPS ethers can be selectively cleaved
