125158-55-6Relevant articles and documents
Synthesis of 2-acetamido-2,5-dideoxy-5-phosphoryl-dglucopyranose derivatives: New phospha-sugar analogs of N-acetyl-D-glucosamine
Hanaya, Tadashi,Kawaguchi, Masahiro,Sumi, Masakazu,Makino, Kazuo,Tsukada, Keiko,Yamamoto, Hiroshi
, p. 1147 - 1165 (2013/08/23)
Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-Obenzyl- 2-deoxy-β-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-Dglucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5- dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).
Synthesis of 2-acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol and -D-glucitol for evaluation as glycosidase inhibitors
Croucher, Paul D.,Furneaux, Richard H.,Lynch, Gregory P.
, p. 13299 - 13312 (2007/10/02)
The title compounds, galacto-1 and gluco-2, were synthesised from N-acetyl-D-glucosamine via a common 1,4-diol intermediate that underwent transformations involving either a single or double inversion of stereochemistry at C-4, respectively. In the double
A facile two-step synthesis of N-acetylmuramic acid by selective functionalization of HO-3 of 2-acetamido-2-deoxy-D-glucose
Merten, Hans,Brossmer, Reinhard
, p. 144 - 149 (2007/10/02)
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