Pyridine → allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranoside

HRID 962424Notes

Reaction equation

HRID 962424 reaction equation
[OH:1][CH:2]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:3]1[NH:12][C:13]([CH3:15])=[O:14].CC(O[C:20]([CH3:22])=[O:21])=O.[CH2:23]([OH:26])[CH:24]=C.B(F)(F)F.CC[O:33][CH2:34][CH3:35].N1C=C[CH:39]=[CH:38][CH:37]=1>C[N+]([O-])=O>[C:13]([NH:12][C@H:3]1[C@@H:4]([O:5][C:23](=[O:26])[CH3:24])[C@H:6]([O:7][C:34](=[O:33])[CH3:35])[C@@H:8]([CH2:10][O:11][C:20](=[O:21])[CH3:22])[O:9][C@@H:2]1[O:1][CH2:39][CH:38]=[CH2:37])(=[O:14])[CH3:15]

Participants

7

Reactant 5

HCID 1049PyridineHCID 7858Allyl AlcoholHCID 7918Acetic AnhydrideHCID 8000Boron trifluoride etherateHCID 439281N-Acetyl-D-Mannosamine

Product 1

HCID 13968146allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranoside

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A solution of ManNAc (5.0 g, 2.6 mmol), and Ac2O (10 mL). in pyridine (20 mL) was stirred for 10 hours at room temperature, and the mixture was concentrated, followed by coevaporation with toluene. A solution of the residue, allyl alcohol (2.63 g, 45.2 mmol; 3.1 mL), BF3.OEt2 (1.60 g, 11.3 mmol; 1.39 mL) in CH3NO2 (150 mL) was gently refluxed for 2.5 hours. After cooling, the mixture was concentrated. The residue was chromatographed on silica gel, with toluene-EtOAc (1:2) to give allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranoside in 6.47 g (74 percent);

Workup

  1. concentrationthe mixture was concentrated
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customThe residue was chromatographed on silica gel, with toluene-EtOAc (1:2)

Sources & evidence

ORD record
ord-a2740e9f921043558c37ccda9c52aa6f
Source dataset
uspto-grants-1998_06
Patent number
US05759823

Reaction notes

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