1975
DOI: 10.1016/s0040-4039(00)72177-0
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Darstellung von 2-azido-2-desoxy-d-glucopyranose und z, 4-diazido-2,4-didesoxy-d-glucopyranose

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Cited by 25 publications
(9 citation statements)
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“…In our hands attempts at direct aminolysis of 7 using methanolic ammonia, or using sodium azide and ammonium chloride (in DMF at 140 °C) both failed, however, success with these reactions have been reported by others. 49 An alternative approach to 8 using reaction of iodide 6 with excess teteramethylguanidium azide in DMF (120 °C, 3 days) is known from the literature. 25 The structure of azide 8 was confirmed by X-ray crystallography.…”
Section: Resultsmentioning
confidence: 99%
“…In our hands attempts at direct aminolysis of 7 using methanolic ammonia, or using sodium azide and ammonium chloride (in DMF at 140 °C) both failed, however, success with these reactions have been reported by others. 49 An alternative approach to 8 using reaction of iodide 6 with excess teteramethylguanidium azide in DMF (120 °C, 3 days) is known from the literature. 25 The structure of azide 8 was confirmed by X-ray crystallography.…”
Section: Resultsmentioning
confidence: 99%
“…1 ) and its derivatives (e.g., 2 and 3 ) are of great interest due to their integral role in bacterial cell wall recycling [ 1 2 ] and the induction of antibacterial resistance [ 3 ]. Numerous syntheses of 1 have been carried out, including early synthetic work by Sinaÿ [ 4 – 5 ] and Paulsen [ 6 7 ], and more recent syntheses by Mobashery [ 8 ], Fukase [ 9 ], and Mark [ 10 ], which have enabled further studies in the field of antibacterial research.…”
Section: Introductionmentioning
confidence: 99%
“…Levoglucosan, however, readily allows a combination of the functionalisation at C(4) and the substitution of HOÀC(2) by an azido group [15]. We decided to use the anhydrogalactose 7 as starting material.…”
mentioning
confidence: 99%
“…Epoxide-ring opening with NaN 3 and NH 4 Cl in boiling EtOH/H 2 O [15] [17] gave the gluco-azide 11 (73%). This was reduced to the amine 12 (71 ± 77%) with LiAlH 4 in THF or Mg/I 2 in MeOH.…”
mentioning
confidence: 99%
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