Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside, and alkaloid derivatives

A New Lead Identification Strategy: Screening an sp3‐rich and Lead‐like Compound Library Composed of 7‐Azanorbornane Derivatives

“…These alkynes were modified with easily available azides to furnish triazoles endo ‐ 6 a – 6 i and exo ‐ 6 a – 6 i . To circumvent the handling of dangerous low molecular weight azides (i.e., 2‐azidoethanol and 3‐azidopropanol), the hydroxy group‐bearing triazoles 6 j and 6 k were synthesized by cleaving the tert ‐butyldimethylsilyl groups of 6 h and 6 i using SO 3 H silica gel according to our previous reports …”

“…These isomerso fa lkynes weree asily separableb ys ilica gel columnc hromatography.D eprotection of the N-Boc group of the each isomer and the subsequent Nmethylation gave alkynes endo-5 and exo-5.T hese alkynes were modified with easily available azides to furnisht riazoles endo-6a-6i and exo-6a-6i.T ocircumvent the handling of dangerouslow molecular weight azides (i.e., 2-azidoethanol and 3azidopropanol), the hydroxy group-bearing triazoles 6j and 6k were synthesized by cleaving the tert-butyldimethylsilyl groups of 6h and 6i using SO 3 Hs ilica gel according to our previous reports. [21,22] Molecular parameters of the library components Molecular parameters of the triazoles are shown in Table 1. The Fsp 3 values of all the synthesized compounds 6a-6k were Figure 1.…”

A Greener Technique for Microwave-Assisted O-Silylation and Silyl Ether Deprotection of Uridine and Other Substrates

“…In addition, the traditional THF/water/acid procedures usually suffer from lengthy reaction times, especially for bulkier silyl ethers such as TBS, TBDPS, or TIPS [30]. Some more environmentally friendly methods for silyl ether cleavage include examples with catalytic copper (II) salts [31,32], catalytic I 2 [14,33], SO 3 H silica gel [34], alumina [35,36] kaolinite [37] and montmorillonite K-10 clay catalysis [38].…”