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

HRID 564897Notes

Reaction equation

HRID 564897 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.[O:31]([CH2:34][CH3:35])CC.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:31])[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

8

Reactant 6

HCID 1049PyridineHCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 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 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&Circlesolid;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-66bddea7bb3f4888bdda52725ed90a81
Source dataset
uspto-grants-2001_01
Patent number
US06168934A

Reaction notes

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