The use of tetramethylguanidinium azide in non-halogenated solvents avoids potential explosion hazards
Tetramethylganidinium azide was used in the efficient synthesis of glycosyl azides and steroidal azides in non-halogenated solvents, thereby avoiding potential explosion hazards.
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Cited by (29)
A synthesis of cephalostatin 1
2019, TetrahedronCitation Excerpt :Having been extensively investigated and used by Fuchs et al. the pyrazine synthesis was easy to perform, as illustrated in Scheme 15 [35]. Adjacent to the easily enolized C3 ketone, the C2 of south part 42 was easily brominated by treating with phenyltrimethylammonium tribromide (PTAB) in THF, and substitution of the resultant α-bromo ketone with tetramethylguanidinium azide (TMGA) in MeNO2 [97] provided the α-azido ketone 101 in good yield. In a similar way, we prepared the α-amino methoxime 102 in good yield through a sequence involving bromination at the C2 of 6 with PTAB, substitution with sodium azide in DMF, formation of the C3 methoxime with O-methylhydroxylamine, and Staudinger reduction of the azide group.
Synthesis and Transformation of Glycosyl Azides
2006, Advances in Carbohydrate Chemistry and BiochemistryCitation Excerpt :For the direct formation of glycosyl azides from peracylated saccharides, the latter can be first transformed by trimethylsilyl iodide into the glycosyl iodides, which in turn show an increased reaction rate.133,134 With trimethylsilyl azide or tetramethylguanidinium azide135,136 the familiar 1,2-trans glycosyl azides are obtained. An exception was reported in the treatment of 2,3,4-tri-O-benzyl-α-l-fucopyranosyl iodide (110) with (insoluble) NaN3 in dichloromethane, which gave the α-azide 111 under retention of configuration.138
Stereoselective synthesis of 1,2-cis- and 2-deoxyglycofuranosyl azides from glycosyl halides
2000, Carbohydrate ResearchCitation Excerpt :Glycosylation of 5α was reported to occur with inversion at the anomeric position and competing concomitant anomerisation to the more reactive β-chloride. The latter process apparently reduced the selectivity of glycosylation and was especially sensitive to solvent effects [11]. Therefore, a number of displacement experiments of 5α with different azide donors were carried out in order to find proper inversion conditions.
On the relationship of OSW-1 to the cephalostatins
1999, Bioorganic and Medicinal Chemistry Letters