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Sulfur trioxide-pyridine complex is used for sulfations of alcohols, sulfonations, deoxygenations and other reductions, oxidations with dimethyl sulfoxide. It is also used as a source of sulfur trioxide especially in the preparation of sulfate esters. Further, it is used as an activating electrophile in a Parikh-Doering oxidation. In addition to this, it is also used in the preparation and anticoagulation test of sulfated silk fibroin.
Converts alcohols to monoalkyl sulfates, utilized in carbohydrate protection: Carbohydr. Res., 127, 211, 131, C8 (1984); J. Org. Chem., 38, 3510 (1973). The pyridinium sulfates of allylic or benzylic alcohols can be deoxygenated in high yields by in situ LiAlH4 reduction in THF: J. Org. Chem., 34, 3667 (1969); Tetrahedron Lett., 4650 (1972); J. Am. Chem. Soc., 93, 7016 (1971).
Sulfonates indole at the 3-position: Tetrahedron, 29, 669 (1973).
The combination with Dimethyl sulfoxide, A13280, is a mild oxidant for alcohols to carbonyl compounds (Parikh-Doering Reagent): J. Am. Chem. Soc., 89, 5505 (1967), avoiding the very low temperatures required for the Swern and similar systems (see Oxalyl chloride, A18012). With chiral alcohols, less racemization occurs at the ɑ-carbon than with Collins' reagent or pyridinium dichromate: Tetrahedron Lett., 23, 807 (1982); J. Org. Chem., 46, 4799 (1981). Nicolaou utilized the system at 0oC to convert an epoxy alcohol to the corresponding aldehyde in the synthesis of hemibrevitoxin B: J. Am. Chem. Soc., 115, 3558 (1993).
In combination with NaI, reduces ɑ-halo ketones to ketones: Synthesis, 59 (1979), and sulfoxides to sulfides: Synthesis, 984 (1979).
Lim, D. K.; Wylie, R. G.; Langer, R.; Kohane, D. S. Selective binding of C-6 OH sulfated hyaluronic acid to the angiogenic isoform of VEGF165. Biomaterials 2016, 77, 130-138.
Sarbova, V.; Koschella, A.; Cheng, F.; Kelly, S. M.; Heinze, T. Studies on the sulfation of cellulose alpha-lipoate and ability of the sulfated product to stabilize colloidal suspensions of gold nanoparticles. Carbohydr. Polym. 2015, 124, 117-123.
Gefahrenhinweise (EU): H302-H314-H318
Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.