Dimethylformamide → L-(-)-Fucose

HRID 1755697Notes

Reaction equation

HRID 1755697 reaction equation
[OH:1][CH:2]1[O:10][C@@H:9]([CH3:11])[C@@H:7]([OH:8])[C@@H:5]([OH:6])[C@@H:3]1[OH:4].CN(C=O)C.OC1O[C@H](C)[C@H](O)[C@H](O)[C@H]1O>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[O:1]=[CH:2][C@H:3]([C@@H:5]([C@@H:7]([C@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4]

Participants

6

Reactant 3

HCID 6228Dimethylformamide2×HCID 171066-Deoxy-L-galactopyranoseHCID 194667724-73-4

Product 1

HCID 3034656L-(-)-Fucose

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 1049PyridineSolvent

Procedure

For example, L-fucopyranose was transformed into a 4'-acetyl-2',3'-O-benzyl-L-fucopyranose following a method described in Dale, J. K. et al., J. Chem. Soc. 52:2534 (1930); and Hockett, R. C. et al., J. Am. Chem. Soc. 61:1658 (1939). See Scheme I in FIG. 12 (DMF=dimethylformamide; DMAP=4-(dimethylamino)pyridine; Bn=benzyl; and pyr=pyridine.). Similarly, D-fucopyranose can be converted to 4'-acetyl-2,3-O-benzyl D-fucopyranose.

Sources & evidence

ORD record
ord-6585c5fbc2f042279fd20a909b6511c4
Source dataset
uspto-grants-1995_08
Patent number
US05438130

Reaction notes

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