TY - JOUR AU - Sapkota, Krishna; Huang, Faqing TI - Selective Protection of Secondary Alcohols by Using Formic Acid as a Mild and Efficient Deprotection Reagent for Primary tert-Butyldimethylsilyl Ethers SN - 0936-5214 SN - 1437-2096 PY - 2019 JO - Synlett JF - Synlett LA - EN VL - 30 IS - 16 SP - 1895 EP - 1898 ET - 2019/03/19 DA - 2019/09/16 KW - selective deprotection KW - TBDMS ethers KW - formic acid KW - secondary alcohol protection KW - desilylation AB - A mild, efficient, and environmentally friendly method for the selective protection of secondary hydroxyl groups is described. The method involves the protection of both primary and secondary hydroxyl groups as tert-butyldimethylsilyl (TBDMS) ethers and selective deprotection of the primary TBDMS group with formic acid in acetonitrile/water. The rates of desilylation of primary and secondary TBDMS ethers by different concentrations of formic acid are determined. Formic acid of 5–20% concentration is found to selectively deprotect primary TBDMS ethers while keeping more than 95% of their secondary counterparts intact. PB - © Georg Thieme Verlag DO - 10.1055/s-0037-1611757 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1611757 ER -