80522-42-5 | Triisopropylsilyl trifluoromethanesulfonate

Packsize	Purity	Availability	Price	Discounted Price
5g	97%	in stock	$8.00	$5.00
25g	97%	in stock	$9.00	$7.00
100g	97%	in stock	$30.00	$21.00
500g	97%	in stock	$115.00	$80.00

Description

• Catalog Number: AB80049
• Chemical Name: Triisopropylsilyl trifluoromethanesulfonate
• CAS Number: 80522-42-5
• Molecular Formula: C10H21F3O3SSi
• Molecular Weight: 306.4176
• MDL Number: MFCD00009913
• SMILES: CC([Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F)C

Computed Properties

• Complexity: 347
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 18
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5

Upstream Synthesis Route

Triisopropylsilyl trifluoromethanesulfonate is a highly versatile reagent commonly used in organic synthesis as a silylating agent. This compound is valued for its ability to selectively protect hydroxyl groups in the presence of other functional groups, making it a valuable tool in complex molecule synthesis. By utilizing Triisopropylsilyl trifluoromethanesulfonate, chemists can introduce the triisopropylsilyl (TIPS) protecting group onto alcohol functionalities, thereby allowing for further manipulation of the molecule while preserving its other reactive sites. This reagent is particularly useful in the synthesis of pharmaceuticals, natural products, and other fine chemicals where the selective modification of hydroxyl groups is crucial for success.

Literature

• Optically pure N-hydroxy-O-triisopropylsilyl-alpha-L-amino acid methyl esters from AlCl3-assisted ring opening of chiral oxaziridines by nitrogen containing nucleophiles.

  The Journal of organic chemistry 20051209

• Toward improving the chemistry of N-acyliminium ions: nucleophilic substitution reactions of pyrrolidinone derivatives with trialkylsilyl nucleophiles catalyzed by triisopropylsilyltrifluoromethane sulfonate (TIPSOTf).

  Organic letters 20050707