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  • Synthesis of alpha-fluorosulfonate and alpha-fluorosulfonamide analogues of a sulfated carbohydrate.

Synthesis of alpha-fluorosulfonate and alpha-fluorosulfonamide analogues of a sulfated carbohydrate.

Organic letters (2006-11-17)
Latifeh Navidpour, Wallach Lu, Scott D Taylor
ABSTRACT

The first synthesis of sulfonamide and sulfonate analogues of a sulfated carbohydrate in which the ester oxygen of the sulfate is replaced with a CHF or CF2 group is reported. This was accomplished by electrophilic fluorination of the protected sulfonate and sulfonamide precursors. [reaction: see text].

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Lithium bromide solution, 54 wt. % in H2O
Sigma-Aldrich
Lithium bromide, AnhydroBeads, −10 mesh, ≥99.9% trace metals basis
Sigma-Aldrich
Lithium bromide, powder and chunks, ≥99.995% trace metals basis
Sigma-Aldrich
Fluorosulfonic acid, purified by triple-distillation
Sigma-Aldrich
Lithium bromide, AnhydroBeads, −10 mesh, 99.999% trace metals basis
Sigma-Aldrich
Lithium bromide, ReagentPlus®, ≥99%