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Deprotections

Classic Method

Nitrogen is central to medicinally-oriented organic synthesis, therefore it is important to be able to protect and deprotect them throughout a synthesis. However, the most useful nitrogen protecting groups, like sulfonamides, which provide high crystallinity are extremely difficult to remove in high yield through simple non-toxic methods.

Diphenyl Sulfonamide Deprotection

N-Allylimidazole Deprotection

Problems

  • Requires highly toxic materials like sodium-mercury amalgam
  • Conditions utilize strong acids at high temperatures
  • Handling of alkali metals and liquid ammonia at cryogenic temperatures
  • Safety and economic issues due to special equipment and disposal needs

SiGNa’s Method

Nitrogen deprotection using SiGNa materials effects clean desulfonation and deallylation utilizing a safe, smooth solution process. The SiGNa method improves yield and reaction conditions, provides milder conditions, and simplifies process purification.

Diphenyl Sulfonamide Deprotection

N-Allylimidazole Deprotection

N-Tosyl Pyrrole Deprotection

Benefits

  • Provides a smooth solution process at room temperature
  • Highly selective allowing more options for substrate functionalization
  • No toxic (i.e. mercury) or hazardous (i.e. liquid ammonia) materials needed
  • No special equipment required for handling or processing

Recommended Products for Deprotections

Alkali Metal-Silica Gel

Highly loaded, free-flowing stabilized alkali metal powders with reactivity as high as the parent metal.

Alkali Metal-Alumina Gel

Highly loaded, atomically dispersed alkali metal powder (includes lithium) wtih more extensive reactivity than the parent metal.

New Discoveries

Currently SiGNa is working on the next element in the alkali metal family, Lithium. A number of new discoveries have been made. Read More

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