78539
Boc-Tyr(Allyl)-OH
≥98.0% (HPLC)
Synonym(s):
Boc-O-allyl-L-tyrosine
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About This Item
Empirical Formula (Hill Notation):
C17H23NO5
CAS Number:
Molecular Weight:
321.37
UNSPSC Code:
12352209
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3624582
InChI key
YIRRNENSHUFZBH-AWEZNQCLSA-N
SMILES string
CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCC=C)cc1)C(O)=O
InChI
1S/C17H23NO5/c1-5-10-22-13-8-6-12(7-9-13)11-14(15(19)20)18-16(21)23-17(2,3)4/h5-9,14H,1,10-11H2,2-4H3,(H,18,21)(H,19,20)/t14-/m0/s1
assay
≥98.0% (HPLC)
form
powder
reaction suitability
reaction type: Boc solid-phase peptide synthesis
application(s)
peptide synthesis
storage temp.
2-8°C
Quality Level
Application
Due to gem-dimethyl substituent effect, Boc-Tyr(Allyl)-OH is found to be resistant to Claisen rearrangement in water.
Other Notes
Allyl group side-chain protected tyrosine; building block for unnatural amino acids by metathesis reaction
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Aromatic Claisen Rearrangements of O?Prenylated Tyrosine and Model Prenyl Aryl Ethers: Computational Study of the Role of Water on Acceleration of Claisen Rearrangements.
Osuna S, et al.
European Journal of Organic Chemistry, 2013(14), 2823-2831 (2013)
Angewandte Chemie (International Edition in English), 114, 2964-2964 (2002)
A Loffet et al.
International journal of peptide and protein research, 42(4), 346-351 (1993-10-01)
Allyl and allyloxycarbonyl groups are used for the side-chain protection of amino acids. The protecting groups may be selectively cleaved using the reagent HSnBu3 under palladium catalysis. The preparation of Boc and Fmoc series of protected amino acids is described.
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