Zur stereoselektiven Synthese von 2‐O‐Benzyl‐1‐O‐hexadecyl‐sn‐glycerol

Abstract

Due to the versatility of 2-0-benzyl-1-0-hexadecyl-sn-glycerol (7) as building block for various alkyl ether lipids and alkyl ether lyso-lipids, 7 was prepared from D-mannit following two different strategies. The final product 7 was obtained either via the intermediate 1,2-O-isopropylidene-sn-glycerol (1) or via 3,4-O-isopropylidene-~-mannit (8) in an overall yield of 6% or 11%, respectively.

Structure–property relationships in a series of diglycerol tetraether model lipids and their lyotropic assemblies: the effect of branching topology and chirality

“…Since the trityl residue is very bulky, the yields during the deprotonation and alkylation steps are quite moderate and, hence, we used a regioselective benzylation of the dibutylstannylene derivatives of the 3-O-alkyl-sn-glycerols 17 instead. 19 However, beside the desired 3-O-alkyl-1-O-benzyl-sn-glycerols 18 the 3-Oalkyl-2-O-benzyl regioisomers were formed. But, both compounds could be fully separated by column chromatography using chloroform-diethyl ether as the eluent and the gradient technique.…”

Novel Trifluoromethyl Ketones as Potent Gastric Lipase Inhibitors

“…1‐(Benzyloxy)‐3‐dodecyloxypropan‐2‐ol 17 (3) : Yield: 12 g (40 %); 1 H NMR: δ= 7.35 (m, 5 H; C 6 H 5 ), 4.60 (s, 2 H; C H 2 C 6 H 5 ), 4.00 (m, 1 H; CHOH), 3.75–3.38 (m, 6 H; 3×CH 2 O), 1.62 (m, 2 H; C H 2 CH 2 O), 1.42–1.18 (m, 18 H; 9×CH 2 ), 0.88 (t, J= 6.2 Hz, 3 H; CH 3 ) ppm; 13 C NMR: δ= 137.9, 128.2, 127.5, 127.2, 73.2, 71.7, 71.5, 71.3, 69.4, 31.8, 29.5, 25.9, 22.5, 14.0 ppm; MS (FAB): m / z (%): 373 (100) [ M +Na] + , 351 (32) [ M +H] + ; elemental analysis calcd (%) for C 22 H 38 O 3 (350.5): C 75.38, H 10.93; found C 75.14, H 10.99.…”