Synthesis of Amino‐L‐Lyxose Phosphonates as Fucosyl‐Phosphate Mimics

Abstract

Some reactions of nitrone 4 are described, namely the nucleophilic addition of dialkyl phosphites, HOP(OR)2, 5a–c or of diethyl methylphosphonate 8 and the dipolar [2+3] cycloaddition of vinylphosphonate 11. Chemical transformations led to 4‐amino‐L‐fucose derivatives bearing a phosphonate group in the 1α position linked to the pyrrolidine ring through a chain of 0–2 carbon atoms. The target compounds proved to be good‐to‐excellent α‐L‐fucosidase inhibitors. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Enzymes for the biocatalytic production of rare sugars

“…Starting material for glycoconjugate vaccines against diseases caused by Shigella sonnei [56] Cytostatic and cytotoxic properties with regards to neoplastic cells (cancer therapy) [1] L-Gulose Building block of bleomycin A 2 , a glycopeptide antibiotic (potential anticancer agent) [18,113] Synthesis of nucleosides that exhibit very potent activity against HBV and HIV [18] Starting material for the production of L-nucleoside-based antiviral medications [113] L-Idose Derivatives are required in the synthesis of sensitive substrates for a-L-iduronidase [18] Derivatives are used as glycosyl donors in the synthesis of heparin oligosaccharides [108] L-Lyxose Component of the antibiotic avilamycin A [33] Potential L-fucosidase inhibitor [11] L-Mannose Component of steroid glycosides [38] L-Psicose…”

Syntheses and Biological Activities of Iminosugars as α-L-Fucosidase Inhibitors

“…N-protection of 37 and radical fragmentation with AIBN and Bu 3 SnH furnished 38. Subsequent acidic deprotection gave phosphonate 35 [29].…”

Tactics and strategies for the synthesis of iminosugar C-glycosides: a review

“…The major isomer (endo-5P) was converted in six steps into phosphonate 128 (see Scheme 100). 152 By contrast, the cycloaddition of nitrone 122 with diethyl allylphosphonate was completely regio-and stereoselective, leading to the exo-anti cycloadduct 129a. The reaction was also successful with an ethyl uridin-5-yl allylphosphonate; the resulting cycloadduct 129b was elaborated into an analogue of UDP-galactofuranose in which the Galf unit is replaced by an iminogalactitol and the …”