Synthesis of Stable Analogues of Glyceroglycolipids

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Synthesis of Stable Analogues of Glyceroglycolipids

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Politecnicodi Milano, Via Mancinelli7,20131 Milano Italy

di Chimica e Biochimica“GiulianaRonzoni”,V. G. Colombo81,20133 Milano, Italy

Stable C-glycosidic analogues of 2-O-(~-D-glucopyranosyl) -srz-glycerol(la), 2-O-(~-Dgatactopyranosyl)-sn-glycerol (lb), l-O-(~-D-glucopyranosyl)-wr-glycerol(7) and their dipalmitoyl ester have been synthesisedstarting from the corresponding2,3,4,6-tetra-O-lxmzyl-glyconolactoncs 9. The 2-O-derivatives 1 were obtained by methylenationof the Iactone 9, reaction of the obtained glycocxoenitol10 with a malonyl radical, reduction of the malonyl derivative 11 and deprotection. The l-O-derivative 7 was obtained by reaction of the Iactone 9 with butenylmagnesiumbromide, reductionof tfreobtainedlactol 14, osmylationand deprotection.O 1997Elsevier Science Ltd.

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Usual work-up refers to dilution with an organic solvent, washing with water to neu~ality drying and evaporation under reduced pressure.

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14.0 (q), 31.1 (t), 48,8 (d), 61.3 (t), 68.9 (t), 73.5 (t), 74.9 (t), 75.1 (t), 75.5 (t), 76.9 (d), 78.4 (d), 79.0 (d), 82.2 (d),

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CDC13) 812,0 (q), 30.0 (t), 47.0 (d), 59.0 (t), 67.0 (t), 67.0 (d), 70.0 (1), 71.0 (t), 73.0 (t), 72.5 (d), 75.0 (d),

H

75.5 (d), 83.0 (d), 170.0 (s). Anal. Calcd for C1,HA,O,: C, 72.39

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%

C

% H T

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% o 1

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2 o 1

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1 i a

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1 o 7

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an hydroscopic solid. 13C NMR (75.43 MHz, DZO), for the predominant

% H

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2H20: C, 41.64 ?ZO; H, 8.39 %. Found: C, 41.42 %; H, 8.54 %.

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