An Improved Procedure for the Preparation of the Garner Aldehyde and Its Use for the Synthesis ofN-Protected 1-Halo-2-(R)-amino-3-butenes

A convergent approach for the synthesis of fluorinated sphingosine analogues

“…Extraction with ether (2x60 mL), drying (MgSO 4 ) and evaporation of the solvent under reduced pressure furnished a colourless oil. Purification by column chromatography (diethyl ether: hexane, 1:4) afforded 9 as a colourless liquid (630 mg, 90%), the spectroscopic data for which were fully consistent with those reported; 11 [α] D = +14.5˚ (c=1.0 CHCl 3 ) (lit. 11 +15.6˚).…”

“…Garner's aldehyde 8 was easily prepared following the literature procedure. 11 The yield from L-serine was 45% with an [α] D = -92 o (c = 1.00, CHCl 3 ) matching literature data. Direct conversion of aldehyde 8 into allylsilane 7 was first attempted using the Wittig-Seyferth reaction.…”

Synthesis of a Novel Ceramide Analogue and its Use in a High‐Throughput Fluorogenic Assay for Ceramidases

“…[34][35][36] The conversion of this aldehyde into the desired epoxide (4S,1'S)-2 was carried out by using dimethylsulfonium methylide to give 60 % yield. [37] As reported by Moore and Luzzio, [37] the required S configuration of the newly formed stereogenic center results from a si face attack of the ilyde on the aldehyde carbonyl group.…”

Synthesis of Thioesters by Simultaneous Activation of Carboxylic Acids and Alcohols Using PPh3/NBS with Benzyltriethylammonium Tetrathiomolybdate as the Sulfur Transfer Reagent

“…[18] It seemed logical to attempt a one-pot conversion of N-Boc serine into Sprotected cysteine by using our methodology involving reagent 1. Accordingly, the reaction of N-Boc--serine methyl ester [19] (29) with benzoic acid and reagent 1 under the reaction conditions (CHCl 3 , 28°C, 2 h) led to the formation of cysteine derivative 30 in 70 % yield (Scheme 6). …”