767042
3-Nitro-1H-1,2,4-triazolide sulfonyl resin
General description
1% DVB
Particle Size: 100-200 mesh dry
Substitution level: 1.0-2.0 mmol/g
MSNT equivalent supported on a polystyrene core.
Particle Size: 100-200 mesh dry
Substitution level: 1.0-2.0 mmol/g
MSNT equivalent supported on a polystyrene core.
Application
Mainly used for esterifications of amino acids with very low racemization.
It is well-known that several amino acids (as His, Cys, Asn, and Asp) are sensitive toward esterification mainly due to the
racemization of the CHα. The standard carbodiimide/DMAP method gives high racemization. This is why some special
coupling reagents have been designed to lower racemization overtime even with mild bases (as N-methylimidazole) as
MSNT (1-(Mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole) and DCBC (2,6-Dichlorobenzoyl chloride). This resin offers
all the advantages of MSNT on a solid-support whereas its former sulfonyl chloride counterpart is giving high
racemization.
It is well-known that several amino acids (as His, Cys, Asn, and Asp) are sensitive toward esterification mainly due to the
racemization of the CHα. The standard carbodiimide/DMAP method gives high racemization. This is why some special
coupling reagents have been designed to lower racemization overtime even with mild bases (as N-methylimidazole) as
MSNT (1-(Mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole) and DCBC (2,6-Dichlorobenzoyl chloride). This resin offers
all the advantages of MSNT on a solid-support whereas its former sulfonyl chloride counterpart is giving high
racemization.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Sieber, P.
Tetrahedron Letters, 28, 6147-6150 (1987)
Blankemeyer-Menge, B.;
Tetrahedron Letters, 31, 1701-1704 (1990)
Zander, N.;
Tetrahedron Letters, 42, 7783-7785 (2001)
CGerhardt, J.;
Tetrahedron Letters, 44, 6557-6560 (2003)
Zander, N.; et. at.
Organic Syntheses, 81, 235-235 (2005)
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