129217-24-9Relevant articles and documents
Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks
Alex, Catherine,Visansirikul, Satsawat,Zhang, Yongzhen,Yasomanee, Jagodige P.,Codee, Jeroen,Demchenko, Alexei V.
, (2020/01/03)
Reported herein is the synthesis of a number of building blocks of 2-amino-2-deoxy-D-mannose from common D-glucose precursors.
A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction
Xing, Shuo,Gleason, James L.
, p. 1515 - 1520 (2015/01/30)
A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy hinges on the alkylation of benzylidene-protected glucal with 2-bromopropionic acid and thus circumvents a challenging and non-reproducible SN2 step at the C-3 position of glucosamine derivatives. The subsequent sequence includes an azidonitration and an unusual azide reduction/acylation step via an aza ylide/oxaphospholidine intermediate. This approach generates a protected N-glycolyl MDP that can be either subjected to a one-step global deprotection or differentially deprotected to obtain further derivatives.
Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis
Henderson, Alexander S.,Bower, John F.,Galan, M. Carmen
supporting information, p. 9180 - 9183 (2015/02/19)
Versatile syntheses of C2-linked and C2-symmetric carbohydrate-based imidazol(in)ium salts from functionalised amino-carbohydrate derivatives are reported. The novel NHCs were ligated to [Rh(COD)Cl]2 and evaluated in Rh-catalysed asymmetric hydrosilylation of ketones with good yields and promising enantioselectivities.