GlyTouCan:G23553KL → 2-deoxy-2-fluoro-4-O-formyl-D-ribose
Reaction equation
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].[F:18][C@@H:19]1[C@H:25]([OH:26])[C@@H:24]([CH2:27][OH:28])[O:23][CH:21]([OH:22])[C@@H:20]1[OH:29]>C(O)(=O)C>[F:18][C@H:19]([C@@H:25]([C@@H:24]([CH2:27][OH:28])[O:23][CH:21]=[O:22])[OH:26])[CH:20]=[O:29]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In step 2, compound (2) obtained in step 1 above is dissolved in acetic acid and oxidized with lead tetraacetate at room temperature to cause an oxidative cleavage of the α-glycol of 3-deoxy-3-fluoro-D-allopyranose, whereby the 2-carbon atom forms a formyl group. Thus, 2-deoxy-2-fluoro-4-O-formyl-D-ribose is formed as the oxidative product, which is then heated at 70°-90° C. in an aqueous solution under an acidic condition for the elimination of O-formyl group, whereby a ring-closing reaction occurs again to form 2-deoxy-2-fluoro-α,β-D-ribofuranose [compound (3)]. In the next step 3, compound (3) above is reacted with methanol in hydrogen chloride-methanol at room temperature for methylglycosidation, whereby forming a mixture of methyl 2-deoxy-2-fluoro-α-D-ribofuranoside [compound (4)] and methyl 2-deoxy-2-fluoro-β-D-ribofuranoside [compound (5)].
Sources & evidence
- ORD record
- ord-14a8df49f6764344a39ebce6e049f7b6
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05773607
Reaction notes
Loading…