A MILD AND FEASIBLE DEPROTECTION OF ALCOHOL TETRAHYDROPYRANYL OR METHOXYMETHYL ETHERS CATALYZED BY Sc(OTf)₃

Bismuth(III) Triflate in Organic Synthesis

“…[73] However, the experimental conditions seem to be more drastic than the ones reported with Sc(OTf) 3 , which catalyses this transformation at room temperature. [74] Scheme 40…”

Silica Triflate as a New, Mild and Efficient Catalyst for Tetrahydropyranylation of Alcohols and Deprotection of Tetrahydropyranyl Ethers

“…A variety of reagents have been used for tetrahydropyranylation and detetrahydropyranylation, e. g., ZrCl 4 , 1 I 2 , 2 LiBr, 3 PdCl 2 (CH 3 CN) 2 , 4 Wells-Dawson heteropolyacid, 5 Fe(ClO 4 ) 3 , 6 sulfuric acid supported on silica gel, 7 potassium dodecatungstocobaltate trihydrate, 8 DDQ, 9 PPh 3 Br 2 , 10 ion exchange resins, 11 BF 3 .OEt 2 , 12 acetyltriphenylphosphonium bromide, 13 and electrogenerated acid. 14 More recently, Sc(OTf) 3 , 15 [Ru(CH 3 ) 3 (triphos)](OTf) 2 , 16 LiOTf, 17 In(OTf) 3 18 and Bi(OTf) 3 19 have also been employed for this purpose. Although these methods are satisfactory for many molecules, some have limitations, such as the use of expensive and toxic reagents, high temperature, long reaction times, incompatibility with other acid-sensitive functional groups, and nonreusability.…”

Synthesis and antifungal properties of papulacandin derivatives

“…Finally, removal of the MOM group proved to be a challenge. The use of Dowex (50 × 8) acidic resin in dry MeOH gave the most consistent results, but also the use of Sc(OTf) 3 in dry acetonitrile in the presence of 1,3-propanediol [ 49 ] yielded the deprotected product. The final compounds were purified by preparative HPLC.…”