A12202 Sulfur trioxide-pyridine complex, 98%, active SO3 ca 48-50%

Sulfur trioxide-pyridine complex, 98%, active SO3 ca 48-50%

Chemische Eigenschaften

Literaturverweise

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 0^oC 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.