تفاعل #1244280

ord-a65f283d8bfe411c83040c8dda85d283

معادلة التفاعل

CC(=O)N[C@H]1[C@H](O[C@H]2[C@H](O)[C@H]3N=C(C)O[C@H]3O[C@@H]2CO)O[C@H](CO)[C@@H](O)[C@@H]1O
chitobiose oxazoline
CC(=O)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
N,N′-diacetylchitobiose
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O
N-acetyllactosamine
→
C1=NCCO1.CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O
LacNAc oxazoline

المتفاعلات

CC(=O)N[C@H]1[C@H](O[C@H]2[C@H](O)[C@H]3N=C(C)O[C@H]3O[C@@H]2CO)O[C@H](CO)[C@@H](O)[C@@H]1O
chitobiose oxazoline
CC(=O)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
N,N′-diacetylchitobiose
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O
N-acetyllactosamine
—
trisaccharide oxazoline

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

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]

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07807405B2uspto-grants-2010_10