Cronobacter thuringiensis type 5 lipopolysaccharide O-antigen oligosaccharide fragment and preparation method and application thereof
A technology of Cronobacter and lipopolysaccharide, which is applied to the preparation of sugar derivatives, antigen carriers, chemical instruments and methods, etc., can solve problems such as inhomogeneity, and achieve the effects of reasonable design, good purity, and simple separation
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[0076] Example 1: 2-Amino-1-ethyl α-D-glucopyranosyl-(1→2)-[2-nitrogen-acetyl-β-D-glucopyranosyl-(1→3) Preparation of -]-β-L-rhamnopyranosyl-(1→4)-2-nitro-acetyl-β-D-glucopyranoside (CT-1)
[0077] The synthetic route of CT-1, the O-antigen oligosaccharide fragment of Cronobacter zurich type 5 lipopolysaccharide, is as follows:
[0078]
[0079] Reagents and reaction conditions in the above-mentioned synthetic route:
[0080] (a) NIS, TfOH, 1,2-dichloroethane, -30°C, 81%, α:β=1:3;
[0081] (b) Cu(OAc) 2 ,CH 2 Cl 2 ,CH 3 OH, r.t., 88%;
[0082] (c) TfOH,CH 2 Cl 2 ,-78℃, 55%;
[0083] (d) NIS, Ir Complex, THF, H2O, r.t., 78%;
[0084] (e) NIS, TfOH, -100℃, CH 2 Cl 2 ,Et 2 O, 70%, only α;
[0085] (f)i.N 2 h 4 ,CH 3 CH 2 OH,reflux; ii.Ac 2 O, pyridine, r.t.; iii. CH 3 ONa,CH 3 OH,CH 2 Cl 2 , r.t.; vi. Pd(OH) 2 ,H 2 O,CH 3 OH,CH 2 Cl 2 .
[0086] (1) p-tolyl 4-oxo-benzyl-2-oxo-allyl-3-oxo-pyridinecarbonyl-1-thio-α-L-rhamnopyranoside (1)
[0087]Dis...
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