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

411515

Sigma-Aldrich

Lithium bromide solution, 54 wt. % in H₂O

236535

Sigma-Aldrich

Fluorosulfonic acid, purified by triple-distillation

229733

Lithium bromide, powder and chunks, ≥99.995% trace metals basis

429465

Lithium bromide, AnhydroBeads^™, −10 mesh, 99.999% trace metals basis

449873

Lithium bromide, AnhydroBeads^™, −10 mesh, ≥99.9% trace metals basis

213225

Sigma-Aldrich

Lithium bromide, ReagentPlus^®, ≥99%