Hydrogen Bromide → HCID 11132283, compound

HRID 1421356Notes

Reaction equation

HRID 1421356 reaction equation
C(O[CH:5]1[O:14][C@@H:13]([CH3:15])[C@H:12]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[C@@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[F:23])(=O)C.[BrH:24]>C(O)(=O)C>[C:9]([O:8][C@@H:7]1[C@@H:12]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[C@H:13]([CH3:15])[O:14][C@@H:5]([Br:24])[C@@H:6]1[F:23])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 15885012HCID 15885012, compound

Product 1

HCID 11132283HCID 11132283, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound (8) (ie., the mixture of said α- and β-anomers above) is brominated in a conventional manner in solution of hydrogen bromide in acetic acid, to give 3-O-acetyl-2,4,6-trideoxy-2-fluoro-4-(trifluoroacetylamino)-α-L-mannopyranosyl bromide [Compound (9)] of the following formula ##STR16## as a 1-bromo-sugar. By the way, the corresponding 1-iodo-sugar can be obtained by reacting Compound (8) with iodo-trimethylsilane in anhydrous toluene.

Workup

  1. addition, the mixture of said α- and β-anomers above)

Sources & evidence

ORD record
ord-e9953e4b40a942dcb037a33ce0ba9135
Source dataset
uspto-grants-2000_06
Patent number
US06075135

Reaction notes

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