Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues
(2005) In Tetrahedron Letters 46(6). p.991-993- Abstract
- A C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues was synthesized in seven steps from tyrosine tert-butyl ester and a sugar amino acid precursor derived from D-glucosamine. An Fmoc-protected D-glucosamine derivative was oxidized at C-6 to give the sugar amino acid, which was immediately coupled to tyrosine tert-butyl ester to produce an orthogonally protected building block. This building block was subsequently elongated to the trimer via the dimer, and finally cyclized to give the C3-symmetric macrocycle.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/158666
- author
- Billing, Johan LU and Nilsson, Ulf LU
- organization
- publishing date
- 2005
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Tetrahedron Letters
- volume
- 46
- issue
- 6
- pages
- 991 - 993
- publisher
- Elsevier
- external identifiers
-
- wos:000226714000023
- scopus:12344268871
- ISSN
- 0040-4039
- DOI
- 10.1016/j.tetlet.2004.12.038
- language
- English
- LU publication?
- yes
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- 25f42b12-5d86-4cf4-a1cb-13d7be17354e (old id 158666)
- date added to LUP
- 2016-04-01 16:02:35
- date last changed
- 2022-01-28 08:55:15
@article{25f42b12-5d86-4cf4-a1cb-13d7be17354e, abstract = {{A C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues was synthesized in seven steps from tyrosine tert-butyl ester and a sugar amino acid precursor derived from D-glucosamine. An Fmoc-protected D-glucosamine derivative was oxidized at C-6 to give the sugar amino acid, which was immediately coupled to tyrosine tert-butyl ester to produce an orthogonally protected building block. This building block was subsequently elongated to the trimer via the dimer, and finally cyclized to give the C3-symmetric macrocycle.}}, author = {{Billing, Johan and Nilsson, Ulf}}, issn = {{0040-4039}}, language = {{eng}}, number = {{6}}, pages = {{991--993}}, publisher = {{Elsevier}}, series = {{Tetrahedron Letters}}, title = {{Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues}}, url = {{http://dx.doi.org/10.1016/j.tetlet.2004.12.038}}, doi = {{10.1016/j.tetlet.2004.12.038}}, volume = {{46}}, year = {{2005}}, }