Deprotection of t-Butyldimethylsiloxy (TBDMS) Protecting Group with Catalytic Copper (II) Chloride Dihydrate

The protection of functional group is unavoidable in multi-step organic synthesis. Alongwith tetrahydropyranyl (THP) ethers, t-butyldimethylsilyl (TBDMS) ethers have beenwidely used for protecting hydroxyl groups. TBDMS ether is more stable to hydrolysisthan trimethylsilyl ether, but is still readily cleaved by a variety of selective conditionsl.The deprotection of TBDMS is usually under mild acidic conditions [AcOH/H,O/THF,3t l: l', or BF, Et,O/CHCI,', etc. '], or with a fluoride…     

Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N−Ts Bond in a Different Light

Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.     

Simple and Efficient Method for Deprotection of Tetrahydropyranyl Ethers by Using Silica Supported Sodium Hydrogen Sulphate

Tetrahydropyranyl (THP) ethers have been efficiently and simply deprotected by using Silica supported sodium hydrogen sulphate (NaHSO₄‐SiO₂) in methanol at room temperature to regenerate the parent alcohols in high yields.     

Rapid Access to 1-Benzyl 2-Substituted Piperazines: Application to the Synthesis of 1-Benzyl-2-difluoromethyl-Piperazine

A rapid and efficient synthesis of 1-benzyl-2-difluoromethyl-piperazine is herein described. The new pathway has the advantage of avoiding orthogonal protection at the two piperazine nitrogen atoms; therefore it is suitable for access to several 1-benzyl 2-substituted piperazines starting from the simple commercially available N,N′-dibenzylethylendiamine.     

A new type of pH-sensitive phospholipid

We describe the synthesis and characterization of a type of pH-sensitive pentaerythritol phospholipids, using a trialkoxybenzylidene acetal as the acid-labile moiety. This lipid was prepared by an eight-step synthesis via a latentiation strategy. Liposomes were prepared via the thin film extrusion method. The changes of liposomal sizes were measured by dynamic light scattering. Content release rates of the liposomes as a function of pH were monitored by using a calcein fluorescence dequenching assay. These results indicated that this new liposomal system was capable of releasing its contents under mildly acidic conditions. At last, in vitro cytotoxicity was assayed against three cell lines, suggesting this type of phospholipids was low toxic.     

Rapid and efficient protection of alcohols and phenols,and deprotection of trimethylsilyl ethers catalyzed by a cerium‐containing polyoxometalate

Herein, we want to report a simple and convenient way for protection‐deprotection of alcohols in the presence of ammonium decatungstocerate(IV) {(NH₄)₈[CeW₁₀O₃₆]·20H₂O} as catalyst under ambient temperature in CH₃CN. Using 0.002 mmol of the catalyst, various alcohols and phenols were transformed easily to the corresponding TMS ethers in excellent yields. In the second part, various TMS ethers were successfully converted to the parent hydroxyl compounds in the presence of the ammonium decatungstocerate(IV) catalyst. Copyright © 2010 John Wiley & Sons, Ltd.     

An Improved Synthesis of N-Alkoxy-α-Oxo-Arylacetamides

The title compounds can be prepared in good yields in a one-pot procedure from arylglyoxylic acid chlorides, 2-pyridone and O-alkylhydroxylamines.     

A Convenient Synthesis of Chiral,Non-Racemic [4aS,8aR]-5,5,8a-Trimethyl Octahydro-2,2-(1,3-Dioxolane)-Naphthalene

(-)-(4aS,8aR)-5,5-8a-trimethyl-trans-decaline 1 was prepared in a stereoespecific synthesis of 4 steps and 38% yield. The key-step involves an asymmetric Robinson annulation via Michael addition of chiral imine.