1096035-40-3Relevant academic research and scientific papers
Concise and efficient synthesis of 2-acetamido-2-deoxy-β-D- hexopyranosides of diverse aminosugars from 2-acetamido-2-deoxy-β-D-glucose
Cai, Ye,Ling, Chang-Chun,Bundle, David R.
experimental part, p. 580 - 589 (2009/06/06)
The furanose acetonide derivative 1 is readily prepared from 2-acetamido-2-deoxy-D-glucose on a large scale without the need for chromatography. Mesylation of 1 provides an efficient, concise, synthetic route to rare 2-acetamido-2-deoxy-β-D-hexopyranosides (2 and 3) via the corresponding methyl 2-acetamido-2-deoxy-3-O-methanesulfonyl-β-D- glucopyranoside and subsequent inversion of configuration by direct displacement or formation of a 3,4-epoxide. Opening of this epoxide by azide provided a direct route to methyl 2-acetamido-4-amino-2,4,6-trideoxy-β-D- gulopyranoside 4. Benzylation of 1 followed by ring expansion to the glucopyranoside, deoxygenation at C-6, and subsequent displacement of a C-4 triflate permitted the synthesis of methyl 2-acetamido-4-amino-2,4,6-trideoxy- β-D-galactopyranoside 5. Methyl 2-acetamido-2-deoxy-β-D- glucopyranoside available from 1 in quantitative yield was readily converted to methyl 2-acetamido-2-deoxy-β-D-galactopyranoside 6 (>60%) by inversion of configuration at C-4. Introduction of a lactyl substituent at C-3 of oxazoline 1 also provides a facile synthesis of the biologically important muramic acid β-glycoside 7. An interesting reaction to convert 2-acetamido-2-deoxyhexopyranosides to the corresponding 2-deoxy-2-tetrazole is also reported.
