17325-85-8Relevant articles and documents
Dispiroketals in synthesis (Part 15): Simultaneous enantioselective and regioselective protection of glycerol by reaction with C2 symmetric (4S,4'S)-dimethyl-bis-dihydropyran
Genicot,Ley
, p. 1275 - 1277 (1994)
Glycerol was simultaneously, enantioselectively and regioselectively protected by reaction with (4S,4'S)-4,4'-dimethyl-3,3',4,4'-tetrahydro-6,6'-bis-2H-pyran to afford a dispiroketal product.
Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**
Cunha, Ana V.,Havenith, Remco W. A.,Holzheimer, Mira,Minnaard, Adriaan J.,Schouten, Stefan,Sinninghe Damsté, Jaap S.
supporting information, p. 17504 - 17513 (2021/07/06)
Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic molecule in organic geochemistry. The 66-membered macrocycle possesses a unique chemical structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.
Synthesis and catalytic evaluation of acidic carbons in the etherification of glycerol obtained from biodiesel production
Chiosso, María E.,Casella, Mónica L.,Merlo, Andrea B.
, p. 107 - 114 (2020/10/29)
In this paper, the catalytic behaviour of carbonaceous system (Ccs) functionalized with –SO3H groups were studied in the etherification of refined (Gly) and crude glycerol (GlyC), with benzyl alcohol (BA). This Ccs was obtained by a synthetic method with low energetic cost in only 24 h. Its catalytic activity and selectivity were studied varying the catalyst percentage (2.5, 5 and 10 wt.%), the initial reactant molar ratio and temperature (between 80 and 120 °C). A very good catalytic performance was achieved (97 % conversion after 360 min of reaction), at 120 °C, Gly:BA = 3:1 and 10 wt.% of Ccs. The high activity can be attributed to high acid site density (6.4 mmol H+/g), that also allowed us to working at lower reaction temperature (100 °C) and with less catalyst concentration (2.5 wt.%), without observing significant loss in BA conversion. Monoether (ME1) was the major product of the reaction with 72 % selectivity. The material can be reused and still gives a notable conversion of BA (about 43 %) after three successive reuses. Finally, the Ccs was active and selective to the desired products in the etherification of crude glycerol (GlyC) derived of biodiesel industry. An important BA conversion (45 %) was obtained only reducing the water content of GlyC and without carrying out any other purification and/or neutralization treatment.
