Diphenylmethylsilyl ether (DPMS): a protecting group for alcohols

Continuous-Flow Alcohol Protection and Deprotection Reactions Catalyzed by Silica-Supported Sulfonic Acid

“…Near-quantitative conversion of alcohol 2 (94%, 1 H NMR) to the desired diphenylmethylsilyl protected alcohol 3d was obtained at a flow rate of 20 μL/min, a concentration of 0.25 M alcohol, and a reaction temperature of 180°C. This result shows that it is possible to react a primary alcohol with a very bulky disilazane under acid-catalyzed continuous-flow conditions to allow for its protection as a bulky silyl ether with a stability that is intermediate between TMS and TBDMS [16].…”

“…Therefore, the possibility of introducing other silyl ethers using this sulfonic acid-catalyzed reaction under continuous-flow conditions was investigated. Commercially available 1,1,3,3-tetramethyl-1,3-diphenylsilazane (TMDPS), upon reaction with an alcohol, protects the alcohol as a dimethylphenyl silyl ether (DMPS) [16]. Like most silyl ethers, DMPS ethers can be cleaved with a fluoride anion source, but interestingly, it can also be selectively removed in presence of a trimethylsilyl (TMS) ether with lithium-naphthalene [17,18].…”

Selective Deprotection of the Diphenylmethylsilyl (DPMS) Hydroxyl Protecting Group under Environmentally Responsible, Aqueous Conditions

“…Since the diphenylmethylsilyl (DPMS) hydroxyl protecting group was introduced, its use has been limited relative to other silyl ether derivatives. Unmasking by fluoride ion, akin to several alternative silicon‐based analogs, affords the corresponding free alcohol quickly in THF at room temperature in the presence of TBAF.…”

“…Secondary alcohols were also deprotected, although there was a noticeable increase in reaction time, likely a steric effect. Diol-containing substrates also exhibited selectivity towards the DPMS ether, as both TBS and Ph-17 4 4-propylphenyl-0 5…”

Polyvinylpolypyrrolidone-Bromine Complex, Mild and Efficient Polymeric Reagent for Selective Deprotection and Oxidative Deprotection of Silylethers

“…This transformation can be carried out by either a conventional two-step procedure, deprotection followed by oxidation of the free alcohol, or by a direct oxidative method. Several methods have been described well in the literatures for the oxidative deprotection of silyl ethers including Jone's reagent CrO 3 /H 2 SO 4 /acetone [3][4][5], Jone's reagent with potassium fluoride [6], chromiumoxide/ pyridine [7][8][9] PCC [8,10], PDC [8], ClCrO 2 (OSiMe 3 ) [11], [(Ph 3 SiO) 2 CrO 2 ] [12], activated DMSO [13,14], NBS [15,16] DDQ [17,18], Ph 3 CBF 4 [19,20], NOBF 4 [21], and Ce(NH 4 ) 2 (NO 3 ) 6 /NaBrO 3 [22]. In this study, the PVPP-Br 2 complex is obtained by simple complexation of bromine with crosslinked poly vinylpolypyrrolidone which can release in situ bromine species in reaction media.…”