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Trialkylsilyl Blocking Agent
Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.
tert-Butyldimethylsilyltrifluoromethanesulfonate; TBS-OTf; t-Butyldimethylsilyltriflate
Boiling Point: 65° / 10
EINECS Number: 274-102-0
Molecular Weight: 264.33
Specific Gravity: 1.151
Flashpoint: 36°C (97°F)
HMIS Key: 3-3-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.3848
Application: Review of synthetic utility.1
Powerful silylation reagent and Lewis acid.2
Excellent promoter for gylcosidations, especially for trichloroacetimidates.3
Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 127-135.
2. Review: Simchen, G. Advances in Silicon Chemistry; JAI Press: Greenwich, Co, 1991; Larson, G. L. Ed., Vol. 1, 189.
3. Roush, W. R. et al. Org. Lett. 1999, 1, 891; and Roush, W. R.; Narayan, S. Org. Lett. 1999, 1, 899.