2-Deoxy-4-O-{2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranosyl}-2-[(1-hydroxyethylidene)amino]hexopyranose → HCID 131728351, compound

HRID 1803803Notes

Reaction equation

HRID 1803803 reaction equation
C[C:2]1[O:10][C@@H:9]2[C@@H:4]([C@@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3NC(C)=O)[C@@H](CO)O2)[N:3]=1.CC(N[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)C(O)O[C@@H]2CO)O[C@H](CO)[C@@H](O)[C@@H]1O)=O.[C:58]([NH:61][C@@H:62]1[C@@H:68]([OH:69])[C@H:67]([O:70][C@@H:71]2[O:79][C@H:78]([CH2:80][OH:81])[C@H:76]([OH:77])[C@H:74]([OH:75])[C@H:72]2[OH:73])[C@@H:66]([CH2:82][OH:83])[O:65][CH:63]1[OH:64])(=[O:60])[CH3:59]>>[CH3:59][C:58]([NH:61][C@H:62]1[CH:63]([OH:64])[O:65][C@H:66]([CH2:82][OH:83])[C@@H:67]([O:70][C@@H:71]2[O:79][C@H:78]([CH2:80][OH:81])[C@H:76]([OH:77])[C@H:74]([OH:75])[C@H:72]2[OH:73])[C@@H:68]1[OH:69])=[O:60].[O:10]1[CH2:9][CH2:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 4395442-Deoxy-4-O-{2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranosyl}-2-[(1-hydroxyethylidene)amino]hexopyranoseHCID 9800166beta-D-galactosyl-(1->4)-N-acetyl-D-glucosamineHCID 10971516HCID 10971516, compound

Product 1

HCID 131728351HCID 131728351, compound

Procedure

To prepare trisaccharide oxazoline 3, the 4′,6′-O-benzylidene group in 15 was selectively removed by treatment with 80% aqueous AcOH at 50 C. The resulting compound 21 was then selectively glycosylated at the 6′-OH position with 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl trichloroacetimidate under the catalysis of TMSOTf to give trisaccharide derivative 23 (76%). De-O-benzoylation of 23 with subsequent O-acetylation afforded the O-acetylated pentenyl glycoside 25. Finally, compound 25 was converted to the oxazoline derivative by treatment with NIS/TESOTf to give 26, which was de-O-acetylated to provide trisaccharide oxazoline 3. On the other hand, the known chitobiose oxazoline 6[15] and the LacNAc-oxazoline 7[16] were prepared from O-acetylated N,N′-diacetylchitobiose and N-acetyllactosamine, respectively, following the reported procedure.[15, 16]

Sources & evidence

ORD record
ord-bb3f7f1627ae4ee3a71c7899ba4cfbeb
Source dataset
uspto-grants-2013_01
Patent number
US08354247B2

Reaction notes

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