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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
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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

functional group

carbonate
nitro

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.[1]
  • A starting material to prepare a cis-butene derivative, which is used as a polymer terminating agent in the synthesis of monotelechelic glycopolymers.[2]

Other Notes

Reagent for the introduction of the TEOC-amino protecting group which can be cleaved by F-[3][4][5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ4248
BCBH8899V
1067472
046978/1
046550/1

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Sigma-Aldrich

160210

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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)
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.
L.A. Carpino et al.
Journal of the Chemical Society. Chemical Communications, 358-358 (1978)
A. Rosowsky et al.
The Journal of Organic Chemistry, 54, 5551-5551 (1989)
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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