A Route to Carbasugar Analogues - Jonathan Clayden - The ...

Experimental section
254nm, dodecamolybdophosphoric acid (PMA) dip, or over iodine.
chromatography was carried out using Fluorochem Davilsil 40-63u 60 Å.
Flash
All reactions were conducted under atmospheric conditions unless otherwise stated.
Where a nitrogen atmosphere is employed, oven-dried glassware was used, and
immediately purged under vacuum before being backfilled with nitrogen whilst still
hot. Microwave reactions were conducted in a Biotage Initiator synthesis system.
Tetrahydrofuran (THF) and diethylether were distilled under nitrogen from sodium,
using a benzophenone indicator. Dichloromethane and toluene were obtained by
distillation from calcium hydride under nitrogen. Triethylamine was distilled from and
stored over potassium hydroxide. Anhydrous dioxane, methanol and
dimethylformamide were used as purchased from Sigma-Aldrich. Water was used as
supplied by United Utilities. Anhydrous dimethylhexahydro-2-pyrimidinone (DMPU)
was used as supplied by Fluka over molecular sieves (product number 41661); methyl
trifluoromethanesulfonate was used as supplied from Fluka (product number 91736).
Petrol refers to the fraction of light petroleum ether boiling between 40-65 °C. All
other solvents and commercially obtained reagents were used as received or purified
using standard procedures. Isopropyllithium was obtained as a solution (c. 0.7 M) in
pentane, s-butyllithium was obtained as a solution (c. 1.3 M) in cyclohexane and n-
butyllithium was obtained as a solution (c. 2.5 M) in cyclohexane. All organolithium
solutions were titrated prior to use against a stirred solution of diphenylacetic acid in
THF at 0 °C.
Numbering conventions in the main body and experimental sections are:
General Procedure 1: Amide synthesis
The acyl chloride (1.0 eq) in CH 2 Cl 2 (2 cm 3 /mmol) was added drop wise over a period
of 2 hr to a stirred solution of the commercially available amine (1.2 eq) in CH 2 Cl 2 (5
cm 3 /mmol) and Et 3 N (2 eq) at 0 °C under a nitrogen atmosphere. The white emulsion
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