TY - JOUR
T1 - New supramolecular host systems. 5. Diacetals and macro-m-cyclophanes of aldaric esters
T2 - Synthesis, stereochemistry and conformational analysis
AU - Jatzke, Harald
AU - Frische, Klaus
AU - Greenwald, Moshe
AU - Golender, Larisa
AU - Fuchs, Benzion
N1 - Funding Information:
AcknowledgmenTtsh.i s work was supportedin part by researchg rantsf rom the Israel ScienceF oundation and the Ministry of Sciencea nd the Arts. Postdoctorafle llowshipsfr om the Minerva Foundation( to H. J.) and from the Konstanz - Tel-Aviv F6rderkreisa nd the Kurt Lion Foundation( to K. F.) and a grant-in-aidfr om the Ministry of Absorption( to L. G.) are gratefullya cknowledgedW. e much appreciate the interesta nd assistanceo f Prof. Richard R. Schmidt( Universityo f Konstanz).
PY - 1997/3/31
Y1 - 1997/3/31
N2 - A general scheme of carbohydrate diacetal systems (Scheme 2) of the 1,3,5,7-tetraoxadecalin (TOD) type is presented. A sequence of reactions starting with dimethyl D-glucarate (4) (Scheme 3) lead to 2,6-diaryl-4,8-di (methoxycarbonyl)-cis-TOD podands (5 and 6) and to the novel dicarbamate macrocycles (8a,b), which constitute the first m-cyclophanes in the carbohydrate (D-gluco) series. The D-gluco-L-ido interconversion by equilibration of the methoxycarbonyl groups in 5, 6 and 9, was examined in the light of a conformational analysis of the methoxycarbonyl group and its anomeric effect in heterocyclic systems, using molecular mechanics techniques (MM3-GE, i.e., MM3 reparametrized for treatment of the gauche effect) and comparing with experimental data.
AB - A general scheme of carbohydrate diacetal systems (Scheme 2) of the 1,3,5,7-tetraoxadecalin (TOD) type is presented. A sequence of reactions starting with dimethyl D-glucarate (4) (Scheme 3) lead to 2,6-diaryl-4,8-di (methoxycarbonyl)-cis-TOD podands (5 and 6) and to the novel dicarbamate macrocycles (8a,b), which constitute the first m-cyclophanes in the carbohydrate (D-gluco) series. The D-gluco-L-ido interconversion by equilibration of the methoxycarbonyl groups in 5, 6 and 9, was examined in the light of a conformational analysis of the methoxycarbonyl group and its anomeric effect in heterocyclic systems, using molecular mechanics techniques (MM3-GE, i.e., MM3 reparametrized for treatment of the gauche effect) and comparing with experimental data.
UR - http://www.scopus.com/inward/record.url?scp=0030930904&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(97)00165-8
DO - 10.1016/S0040-4020(97)00165-8
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AN - SCOPUS:0030930904
SN - 0040-4020
VL - 53
SP - 4821
EP - 4834
JO - Tetrahedron
JF - Tetrahedron
IS - 13
ER -