55628-55-2Relevant academic research and scientific papers
Preparation method of tribenoside
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Paragraph 0025; 0026; 0027; 0032-0034; 0037-0039, (2018/04/02)
The invention discloses a preparation method of tribenoside. The method comprises the following steps: adding monoacetone glucose and a phase transfer catalyst to benzyl chloride, controlling the reaction temperature of a system, adding an inorganic base solution dropwise to obtain a crude product of tribenzyl monoacetone glucose, performing three-stage molecular distillation for purification toobtain high-purity tribenzyl monoacetone glucose, and adding high-purity tribenzyl monoacetone glucose to ethanol hydrochloride to prepare tribenoside. The method has the advantages of simple and efficient synthesis process, reasonable process, high synthesis efficiency and high yield; reaction operation is simple and convenient, tribenoside contains fewer impurities and is higher in purity and content, operation is convenient, and the European pharmacopoeia standards can be met directly.
Wittig approach to carbohydrate-derived vinyl sulfides, new substrates for regiocontrolled ring-closure reactions
Aucagne, Vincent,Tatibou?t, Arnaud,Rollin, Patrick
, p. 1817 - 1826 (2007/10/03)
Reaction of methyl- and phenylthiomethylidene phosphoranes 1 and 2 with a variety of reducing sugars has been explored. Furano-type carbohydrates afforded with good yields the corresponding open-chain vinyl sulfides, whereas pyrano derivatives produced elimination compounds together with the expected vinyl sulfides, depending on the nature of the protective groups.
One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides
Lohman, Gregory J. S.,Seeberger, Peter H.
, p. 7541 - 7543 (2007/10/03)
Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-α-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-α-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.
Peralkylation of Saccharides under Aqueous Conditions
Wang, Hui,Sun, Lihong,Glazebnik, Serge,Zhao, Kang
, p. 2953 - 2956 (2007/10/02)
Treatment of saccharides with sodium hydroxide and alkyl halides in aqueous dimethyl sulfoxide solution offers a very efficient method for the complete alkylation of saccharides in high yields.
Preparation of O-Hydroxyethyl and O-Hydroxypropyl Derivatives of D-Glucose and 2-Acetamido-2-deoxy-D-glucose for Studies of Modified Hyaluronic Acid
Bjurling, Eva,Jansson, Per-Erik,Lindqvist, Bengt
, p. 589 - 595 (2007/10/02)
Some hydroxyethyl and hydroxypropyl derivatives of D-glucose and of 2-acetamido-2-deoxy-D-glucose have been sunthesized for use as reference substances for structural studies of hydroxyethylated and hydroxypropylated hyaluronic acid.Hydroxyethyl and hydroxypropyl substituents were introduced in the 2-O- or 3-O-position of D-glucose and in the 4-O- or 6-O-positions of 2-acetamido-2-deoxy-D-glucose by reaction of suitably protected sugars with either ethylene oxide or propylene oxide.For hydroxyethyl derivatives yields varied between 21 and 74percent and with a substantial portion of the doubly alkylated compounds.For hydroxypropyl derivatives yields varied between 15 and 80percent.Only trace amounts of the doubly alkylated compounds were found.The proportions of the respective derivatives were estimated using GLC-MS.All products were characterized by 1H and 13C NMR spectroscopy.
Diastereoselective Free-Radical Reactions. Part 3. The Methyl Glucopyranos-1-yl and 1,2-O-Isopropylideneglucopyranos-1-yl Radicals: Conformational Effects on Diastereoselectivity
Crich, David,Lim, Linda B. L.
, p. 2209 - 2214 (2007/10/02)
The 3,4,6-tri-O-benzyl-2-O-t-butyldimethylsilyl-1-O-methyl-D-glucopyranos-1-yl and the 3,4,6-tri-O-benzyl-1,2-O-isopropylidene-D-glucopyranos-1-yl radicals are quenched with high selectivity (>25:1) from the α- and β-face, respectively, by t-dodecanethiol
Diastereoselective radical reactions : β-face selective quenching of the 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-D-glucopyranos-1-yl radical
Crich, David,Lim, Linda B.L.
, p. 2565 - 2568 (2007/10/02)
Pyrolysis of 3,4,6-tri-Obenzyl-1-carbomethoxy-1,2-dideoxy-1-phenylsulfonyl-D-glucopyranose provides the corresponding 1-carbomethoxyglucal which reacts with osmium tetroxide to form a gluco-diol. This diol is converted to an acetonide which is saponified
Synthesis of benzyl and allyl ethers of D-glucopyranose
Gent, Patricia A.,Gigg, Roy
, p. 325 - 333 (2007/10/10)
Starting from allyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside as a key intermediate, the following crystalline compounds were prepared: 2-O-allyl-3,4,6-tri-O-benzyl-D-glucopyranose (11) and its p-nitrobenzoate; 2,3,5-tri-O-benzyl-D-arabinofuranose (12) and the corresponding arabinitol; allyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (7); 3,4,6-tri-O-benzyl-D-glucopyranose (8); 2-O-allyl-3,4-di-O-benzyl-D-glucopyranose (17) and its bis(p-nitrobenzoate); and 3,4-di-O-benzyl-D-glucopyranose (19). The p-nitrobenzoates of compounds 11 and 17 are potential intermediates for the synthesis of the glycolipids of the cytoplasmic membranes of Streptococci.
