54623-22-2Relevant articles and documents
C-glycosylation of oxygenated naphthols with 3-dimethylamino- 2,3,6-trideoxy-L-arabino-hexopyranose and 3-azido- 2,3,6-trideoxy-D-arabino-hexopyranose
Brimble, Margaret A.,Davey, Roger M.,McLeod, Malcolm D.,Murphy, Maureen
, p. 787 - 794 (2003)
In connection with studies directed towards the synthesis of the pyranonaphthoquinone antibiotic medermycin, C-aryl glycosides were prepared by C-glycosylation of naphthols with glycosyl donors. Boron trifluoride diethyl etherate proved to be a suitable Lewis acid to promote the C-glycosylation, and use of the azido glycosyl donor proved more successful than using the dimethylamino glycosyl donor. 5-Hydroxy-1,4-dimethoxynaphthalene underwent facile C-glycosylation with two particular glycosyl donors, whereas 3-bromo-5-hydroxy-1,4-dimethoxynaphthalene was not an effective coupling partner with the same glycosyl donors. These studies indicate that subtle steric and electronic effects need to be considered in order to fine-tune C-glycosylations when using highly functionalized glycosyl donors.
Addition of Hydrazoique Acid to Pseudoglycals Stereoselective Synthesis of L-Acosamine and L-Daunosamine
Abbaci, Belgacem,Florent, Jean-Claude,Monneret, Claude
, p. 667 - 672 (2007/10/02)
Methyl and benzyl glycosides and glycal of L-acosamine (3-amino-2,3,6 trideoxy-L-arabino-hexose) have been stereoselectively prepared via 1,4-addition of hydrazoic acid to L-erythro-hex-2-enopyranose as a key step.Inversion of the C-4 configuration of met
CONVENIENT SYNTHESYS OF L-DAUNOSAMINE AND L-ACOSAMINE
Brimacombe, John S.,Hanna, Roderick,Tucker, Leslie C. N.
, p. 419 - 426 (2007/10/02)
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