Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene

Vandana Bhalla; Manoj Kumar; Tetsutaro Hattori; Sotaro Miyano

doi:10.1016/j.tet.2004.05.035

Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene

Vandana Bhalla, Manoj Kumar, Tetsutaro Hattori, Sotaro Miyano

ENG - Biomolecular Engineering

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

30 Citations (Scopus)

Abstract

O,O″- and O,O′-bis(2-aminoethyl)-p-tert-butylthiacalix[4]arenes of anti conformation have been prepared by the reduction of the corresponding O,O″- and O,O′-bis(cyanomethyl) ethers. Their syn-O,O″- and O,O′-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalix[4]arene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O′-disiloxanediyl-bridged O″,O‴- bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes.

Original language	English
Pages (from-to)	5881-5887
Number of pages	7
Journal	Tetrahedron
Volume	60
Issue number	28
DOIs	https://doi.org/10.1016/j.tet.2004.05.035
Publication status	Published - 2004 Jul 5

Keywords

Calixarene
Interconversion
Stereoselective functionalization

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10.1016/j.tet.2004.05.035

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title = "Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene",

abstract = "O,O″- and O,O′-bis(2-aminoethyl)-p-tert-butylthiacalix[4]arenes of anti conformation have been prepared by the reduction of the corresponding O,O″- and O,O′-bis(cyanomethyl) ethers. Their syn-O,O″- and O,O′-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalix[4]arene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O′-disiloxanediyl-bridged O″,O‴- bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes.",

keywords = "Calixarene, Interconversion, Stereoselective functionalization",

author = "Vandana Bhalla and Manoj Kumar and Tetsutaro Hattori and Sotaro Miyano",

note = "Funding Information: This work was supported by JSPS Research for the Future Program and by a Grant-in-Aid for Scientific Research on Priority Areas (No. 14044009) from the Ministry of Education and Technology, Japan. Two of us, V. B. and M. K., are thankful to JSPS, for financial support. V. B. and M. K. are also thankful to D.A.V. College, Managing Committee (New Delhi) and Guru Nanak Dev University, Amritsar, respectively, for granting study leave.",

year = "2004",

month = jul,

day = "5",

doi = "10.1016/j.tet.2004.05.035",

language = "English",

volume = "60",

pages = "5881--5887",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "28",

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T1 - Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene

AU - Bhalla, Vandana

AU - Kumar, Manoj

AU - Hattori, Tetsutaro

AU - Miyano, Sotaro

N1 - Funding Information: This work was supported by JSPS Research for the Future Program and by a Grant-in-Aid for Scientific Research on Priority Areas (No. 14044009) from the Ministry of Education and Technology, Japan. Two of us, V. B. and M. K., are thankful to JSPS, for financial support. V. B. and M. K. are also thankful to D.A.V. College, Managing Committee (New Delhi) and Guru Nanak Dev University, Amritsar, respectively, for granting study leave.

PY - 2004/7/5

Y1 - 2004/7/5

N2 - O,O″- and O,O′-bis(2-aminoethyl)-p-tert-butylthiacalix[4]arenes of anti conformation have been prepared by the reduction of the corresponding O,O″- and O,O′-bis(cyanomethyl) ethers. Their syn-O,O″- and O,O′-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalix[4]arene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O′-disiloxanediyl-bridged O″,O‴- bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes.

AB - O,O″- and O,O′-bis(2-aminoethyl)-p-tert-butylthiacalix[4]arenes of anti conformation have been prepared by the reduction of the corresponding O,O″- and O,O′-bis(cyanomethyl) ethers. Their syn-O,O″- and O,O′-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalix[4]arene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O′-disiloxanediyl-bridged O″,O‴- bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes.

KW - Calixarene

KW - Interconversion

KW - Stereoselective functionalization

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DO - 10.1016/j.tet.2004.05.035

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ER -

Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene

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Keywords

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