Acetic Acid Mixture with Hydrobromic Acid → HCID 10760195, compound

HRID 481291Notes

Reaction equation

HRID 481291 reaction equation
C(O[CH:5]1[O:18][C@@H:17]([C:19]([F:22])([F:21])[F:20])[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@@H:7]([O:8][C:9](=[O:11])[CH3:10])[CH2:6]1)(=O)C.[BrH:23].C(O)(=O)C>>[C:9]([O:8][C@@H:7]1[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:17]([C:19]([F:22])([F:21])[F:20])[O:18][C@@H:5]([Br:23])[CH2:6]1)(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 54533955HCID 54533955, compound

Product 1

HCID 10760195HCID 10760195, compound

Procedure

Step (12'): Compound 77 (the mixture of the aforesaid anomers) is brominated in its solution in hydrogen bromide-acetic acid by a conventional method, whereby there is obtained 3,4-di-O-acetyl-2,6-dideoxy-6,6,6-trifluoro-α-L-lyxo-hexopyranosyl bromide [Compound 78 of the formula ##STR118## as a 1-bromo sugar. While, when Compound 77 is reacted with iodotrimethylsilane in anhydrous toluene, there is produced a corresponding 1-iodo sugar.

Sources & evidence

ORD record
ord-2bbbf2e1697040a1b8533b4fa668f8b0
Source dataset
uspto-grants-1998_08
Patent number
US05789386

Reaction notes

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