p-Nitrophenyl carbonate Wang resin

Resin-bound p-nitrophenyl carbonate esters react readily with amines to provide the corresponding resin-bound carbamate. Leznoff ^[1] was the first to demonstrate the utility of such resins in solid phase synthesis with the preparation of mono-acylated diamines from symmetrical diamines. Similarly, Dressman, et al. ^[2] have used carbamate linked resin-bound amino acid amides to make hydantoins via a base-mediated cyclization/cleavage strategy. Amines linked to p-nitrophenyl carbonate Wang resin possess similar chemical properties to methoxybenzyloxycarbonyl protected amines. The resin-bound carbamate is, therefore, cleaved with TFA or hydrogenolysis to afford the free amine ^[3]. Alternatively, cleavage by reduction with lithium aluminium hydride can be used to generate N-methylamines ^[4], and Raju & Kogan ^[5] have utilized this resin to prepare sulfonamides by acylation of immobilized arylamines and cleavage with LiOH or NaOMe. An analogous p-nitrophenyl carbonate resin prepared from NovaSyn TGA resin was employed as a support for the solid phase immobilization of amidines ^[6]. This resin was also used to synthesize polyamines ^{[7, 8]}, and to immobilize indoles ^[9] and guanidinylating reagents ^[10]. Loading of this resin can be quantified by measuring the release of p-nitrophenolate ^[11].

Associated Protocols and Technical Articles
Protocols for Loading of Peptide Synthesis Resins

Literature references

^[1] D. M. Dixit, et al. (1978) Israel J. Chem., 17, 248.
^[2] B. A. Dressman, et al. (1996) Tetrahedron Lett., 37,937.
^[3] J. R. Hauske, et al. (1995) Tetrahedron Lett., 36, 1589.
^[4] C. Y. Ho & M. J. Kukla (1997) Tetrahedron Lett., 38, 2799.
^[5] B. Raju & T. P. Kogan (1997) Tetrahedron Lett., 38, 3373.
^[5] A. K. Ghosh, et al. (2001) J. Org. Chem., 66, 2161.
^[6] R. Mohan, et al. (1998) Bioorg. Med. Chem. Lett., 8, 1877.
^[7] S. Tomasi, et al. (1998) Bioorg. Med. Chem. Lett., 8, 635.
^[8] N. D. Hone & L. J. Payne (2000) Tetrahedron Lett., 41, 6149.
^[9] A. L. Smith, et al. (2000) Bioorg. Med. Chem. Lett., 10, 2693.
^[10] A. K. Ghosh, et al. (2001) J. Org. Chem., 66, 2161.
^[11] A. Paio, et al. (2003) Tetrahedron Lett., 44, 1867.

Replaces: 01-64-0123

Color (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading / photometric determination of p-nitrophenol released upon treatment with piperidine / DMF: 0.60 - 1.20 mmol/g
Swelling Volume (in DMF): lot specific result
The polymer matrix is copoly (styrene - 1% DVB ), 100 - 200 mesh.

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