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

HRID 233552Notes

Reaction equation

HRID 233552 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>N1C=CC=CC=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:2](=[O:1])[CH3:3])[C@@H:8]([CH2:10][O:11][C:20](=[O:21])[CH3:22])[O:9][C@@H:2]1[O:1][CH2:8][CH:6]=[CH2:4])(=[O:14])[CH3:15]

Participants

6

Reactant 3

HCID 7858Allyl AlcoholHCID 7918Acetic AnhydrideHCID 439281N-Acetyl-D-Mannosamine

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 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-120338c6e35643ec91e004399dce0573
Source dataset
uspto-grants-1997_01
Patent number
US05593887

Reaction notes

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