92748
4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate
≥97.0%, for peptide synthesis
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2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate, TEOC-ONp
C12H17NO5Si
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Quality Level
Assay
≥97.0%
form
crystals
mp
35-40 °C
application(s)
peptide synthesis
storage temp.
2-8°C
SMILES string
C[Si](C)(C)CCOC(=O)Oc1ccc(cc1)[N+]([O-])=O
InChI
1S/C12H17NO5Si/c1-19(2,3)9-8-17-12(14)18-11-6-4-10(5-7-11)13(15)16/h4-7H,8-9H2,1-3H3
InChI key
ZAQWGGKIMQIVGM-UHFFFAOYSA-N
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Application
4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate can be used as:
- A protecting group for an amine in one of the key synthetic steps of kottamide E total synthesis.
- A starting material to prepare a cis-butene derivative, which is used as a polymer terminating agent in the synthesis of monotelechelic glycopolymers.
Other Notes
Reagent for the introduction of the TEOC-amino protecting group which can be cleaved by F-
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Hoppe-Seyler's Zeitschrift fur physiologische Chemie, 362(9), 1289-1292 (1981-09-01)
2-(Trimethylsilyl)ethyl-4-nitrophenyl carbonate has been prepared as a new reagent for the introduction of the 2-(trimethylsilyl)ethyloxycarbonyl group into amino acids or amino acid derivatives. The resulting N alpha-protected amino acids were found to represent suitable intermediates for the synthesis of peptides.
End-labeled amino terminated monotelechelic glycopolymers generated by ROMP and Cu (I)-catalyzed azide--alkyne cycloaddition
Beilstein Journal of Organic Chemistry, 9(1), 608-612 (2013)
The Journal of Organic Chemistry, 54, 5551-5551 (1989)
Chemical communications (Cambridge, England), 49(23), 2296-2298 (2013-02-12)
The first synthesis of kottamide E, a marine natural product containing a 5,6-dibromoindole linked via a (Z)-enamide to an unusual 1,2-dithiolane-containing amino acid, is reported.
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