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92748

Sigma-Aldrich

4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

≥97.0%, for peptide synthesis

Synonym(s):

2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate, TEOC-ONp

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About This Item

Empirical Formula (Hill Notation):
C12H17NO5Si
CAS Number:
80149-80-0
Molecular Weight:
283.35
Beilstein:
4320585
EC Number:
279-406-7
MDL number:
MFCD00042930
UNSPSC Code:
12352108
PubChem Substance ID:
57653487
NACRES:
NA.22

product name

4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate, ≥97.0%

Quality Level

100

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-

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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B Wünsch et al.
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
Okoth R and Basu A
Beilstein Journal of Organic Chemistry, 9(1), 608-612 (2013)
A. Rosowsky et al.
The Journal of Organic Chemistry, 54, 5551-5551 (1989)
L.A. Carpino et al.
Journal of the Chemical Society. Chemical Communications, 358-358 (1978)
Thomas B Parsons et al.
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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