An improved preparation of benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronate

Keglević, Dina; Ljevaković, Djurdjica

doi:10.1016/s0008-6215(00)83718-0

Cited by 22 publications

(10 citation statements)

References 10 publications

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“…- (9), 30 (5), 29 (23), 27 (5), 15 (6). [54] [55]. Eine Losung von 0,536 g (2,76 mmol) 12 [57] und 1,36 g (437 mmol) Tritylchlorid in 10 ml Pyridin wurde 80 Min. unter Riickfluss gekocht.…”

Section: -0-benzoyl-23-di-o-methoxymethyl-56-didesoxy-~-xylo-hex-5unclassified

“…Eine Losung von 0,536 g (2,76 mmol) 12 [57] und 1,36 g (437 mmol) Tritylchlorid in 10 ml Pyridin wurde 80 Min. unter Riickfluss gekocht. Normale Aufarbeitung (Methylenchlorid/Wasser; Pyridin wurde mit Benzol azeotrop abdestilliert) und Chromatographie (15 g, D) ergaben 1,0 g (83%; [55]: 46,5%) kristallines 13, Smp. 107" ([54]: 108-109").…”

Section: -0-benzoyl-23-di-o-methoxymethyl-56-didesoxy-~-xylo-hex-5unclassified

“…Merhyl-2,3, 4-tri-O-benzyl-/l-~-glucopyranosid (15) [55] [56] [79]. Eine Losung von 8 14 mg (l,87 mmol) 13 in 40 ml D M F wurde rnit 746 mg (32 mmol (4, 84,25 (4, 82,17 (4, 77,32 (4, 75,35 (t), 75,06 (d), 74,77 (t) (6), 253 (34), 244 (19), 243 (81), 241 (3, 240 (16), 193 (6), 181 (7).…”

Section: Methyl-6-o-trityl-~-~-glucopyranosid (13)unclassified

“…-'H-NMR. : 7,5-7,2 (m, (4,82,75 (4, 73,33 (t), 72,13 (t), 71,58 (t), 55,32 (4, 50,45 (4, 34,83 ( t ) , 20,18 ( (4,81,65 (4,72,27 (I), 71,83 (t), 69,40 ( t ) , 55,76 (d), 46,32 (4, 34,83 (t), 20,02 (qa). -MS.: 368 (I), 367 ( M t , 3), 348 (l), 338 (I), 325 (9).…”

Section: Den-5'-o-trityl-~-~-ribofuranosy~)amino]-~45-cyc~opentantriolmentioning

confidence: 99%

“…Na2C03-Losung) und Chromatographie (I5 g, bis Tritylverbindungen eluierte B, dann C) ergaben 660 mg (76% bez. 13;[55]: 61,2%) 15, das BUS…”

unclassified

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Carbocyclische Verbindungen aus Monosacchariden. I. Umsetzungen in der glucosereihe

Bernet

Vasella

1979

Helvetica Chimica Acta

338

131

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A method for the preparation of pentasubstituted cyclopentanes from monosaccharides is presented, involving two crucial steps, viz. the reductive fragmentation of 5-bromo-5-deoxyglucosides (such as 10, 17 and 23, see Scheme 3) with Zn or butyl lithium yielding 5,6-dideoxy-hex-5-enoses (such as 11 a.nd 24, see Schemes 3 and 4 ) , and the subsequent cyclization of these hexenoses with N-methyl-or N-(alkoxyalky1)hydroxylamines (via the corresponding nitroines) to form cyclopentano-isoxazolidines (see Scheme 2). Thus, the glucosides 17 and 23 were converted diastereoselectively and in good yields into the cyclopentano-isoxazolidines 27 and 45 (Schemes 5 and 7), which were characterized by their transformation into various derivatives. 27 and 45 were correlated through the common derivative 62. The configuration of the cyclization products were established1 by pyrolysis of the N-oxide 65 to the enol ether 67 (Scheme 10).

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“…- (9), 30 (5), 29 (23), 27 (5), 15 (6). [54] [55]. Eine Losung von 0,536 g (2,76 mmol) 12 [57] und 1,36 g (437 mmol) Tritylchlorid in 10 ml Pyridin wurde 80 Min. unter Riickfluss gekocht.…”

Section: -0-benzoyl-23-di-o-methoxymethyl-56-didesoxy-~-xylo-hex-5unclassified