Acetic Anhydride → allyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-tolylsulfonyl-alpha-D-mannopyranoside

A solution of allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranoside, prepared as described above, (6.46 g, 16.7 mmol) and methanolic NaOMe (2 mL; 1M solution) in MeOH (100 mL) was stirred for two hours at room temperature, and neutralized by addition of Dowex 50W-X8 [H+ ]. After the resin was filtered off, the filtrate was concentrated followed by coevaporation with pyridine. A solution of tolylsulfonyl chloride (3.50 g, 18.3 mmol) in pyridine (20 mL) and CH2Cl2 (30 mL) was added dropwise to a cooled solution of the residue in pyridine (30 mL) and CH2Cl2 (50 mL) at 0°-5° C. over 30 minutes, and the mixture was stirred for 10 hours at room temperature then cooled. Acetic anhydride (30 mL) was added to the mixture, and the mixture was stirred for five hours room temperature. The mixture was concentrated, and the residue was chromatographed on silica gel, with toluene EtOAc (1:2), to give allyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-tolylsulfonyl-α-D-mannopyranoside (3.68 g, 44%);

1. additionneutralized by addition of Dowex 50W-X8 [H+ ]
2. filtrationAfter the resin was filtered off
3. concentrationthe filtrate was concentrated
4. temperaturethen cooled
5. stirringthe mixture was stirred for five hours room temperature
6. concentrationThe mixture was concentrated
7. customthe residue was chromatographed on silica gel, with toluene EtOAc (1:2)

ORD-Eintrag

ord-5d37064695a24f9788dfba2a4cad1079

Quelldatensatz

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05593887