New supramolecular host systems. 41. novel diacetal podands, diazacrowns and cryptands

Klaus Frische; Moshe Greenwald; Eli Ashkenasi; N. Gabriel Lemcoff; Sarah Abramson; Larisa Golender; Benzion Fuchs

doi:10.1016/0040-4039(95)01938-E

New supramolecular host systems. 4¹. novel diacetal podands, diazacrowns and cryptands

Klaus Frische
, Moshe Greenwald
, Eli Ashkenasi
, N. Gabriel Lemcoff
, Sarah Abramson
, Larisa Golender
, Benzion Fuchs

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

New and important key podands bearing the cis-1,3,5,7-tetraoxadecalin (TOD) core are reported, viz., 2,6-di(hydroxymethyl)- (2) and 2,6-di(aminomethyl)-cis-1,3,5,7-TOD (6), which lead to the first diazacrown-TOD compounds (9a) and (9b) and a corresponding cryptand (11) in the series. 9a&b exhibit very good alkali and earth-alkali ion inclusion ability with selectivity for K⁺ and Ba⁺² . Molecular dynamics (Insight/Discover/AMBER) on the crowns and cryptand were performed, including reparametrized MM3-GE calculations. A convincing case for the TOD based hosts was thus established.

Original language	English
Pages (from-to)	9193-9196
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	50
DOIs	https://doi.org/10.1016/0040-4039(95)01938-E
State	Published - 11 Dec 1995
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)01938-E

Cite this

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title = "New supramolecular host systems. 41. novel diacetal podands, diazacrowns and cryptands",

abstract = "New and important key podands bearing the cis-1,3,5,7-tetraoxadecalin (TOD) core are reported, viz., 2,6-di(hydroxymethyl)- (2) and 2,6-di(aminomethyl)-cis-1,3,5,7-TOD (6), which lead to the first diazacrown-TOD compounds (9a) and (9b) and a corresponding cryptand (11) in the series. 9a\&b exhibit very good alkali and earth-alkali ion inclusion ability with selectivity for K+ and Ba+2 . Molecular dynamics (Insight/Discover/AMBER) on the crowns and cryptand were performed, including reparametrized MM3-GE calculations. A convincing case for the TOD based hosts was thus established.",

author = "Klaus Frische and Moshe Greenwald and Eli Ashkenasi and Lemcoff, \{N. Gabriel\} and Sarah Abramson and Larisa Golender and Benzion Fuchs",

year = "1995",

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doi = "10.1016/0040-4039(95)01938-E",

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TY - JOUR

T1 - New supramolecular host systems. 41. novel diacetal podands, diazacrowns and cryptands

AU - Frische, Klaus

AU - Greenwald, Moshe

AU - Ashkenasi, Eli

AU - Lemcoff, N. Gabriel

AU - Abramson, Sarah

AU - Golender, Larisa

AU - Fuchs, Benzion

PY - 1995/12/11

Y1 - 1995/12/11

N2 - New and important key podands bearing the cis-1,3,5,7-tetraoxadecalin (TOD) core are reported, viz., 2,6-di(hydroxymethyl)- (2) and 2,6-di(aminomethyl)-cis-1,3,5,7-TOD (6), which lead to the first diazacrown-TOD compounds (9a) and (9b) and a corresponding cryptand (11) in the series. 9a&b exhibit very good alkali and earth-alkali ion inclusion ability with selectivity for K+ and Ba+2 . Molecular dynamics (Insight/Discover/AMBER) on the crowns and cryptand were performed, including reparametrized MM3-GE calculations. A convincing case for the TOD based hosts was thus established.

AB - New and important key podands bearing the cis-1,3,5,7-tetraoxadecalin (TOD) core are reported, viz., 2,6-di(hydroxymethyl)- (2) and 2,6-di(aminomethyl)-cis-1,3,5,7-TOD (6), which lead to the first diazacrown-TOD compounds (9a) and (9b) and a corresponding cryptand (11) in the series. 9a&b exhibit very good alkali and earth-alkali ion inclusion ability with selectivity for K+ and Ba+2 . Molecular dynamics (Insight/Discover/AMBER) on the crowns and cryptand were performed, including reparametrized MM3-GE calculations. A convincing case for the TOD based hosts was thus established.

UR - https://www.scopus.com/pages/publications/0028892503

U2 - 10.1016/0040-4039(95)01938-E

DO - 10.1016/0040-4039(95)01938-E

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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