€ 48,00*
SIZE
200 - 400 mesh
Capacity
0.8 - 1.5 mmol/g
Product number
H40000.5G
H40000.5G
Product information
These resins are alternatives to the corresponding chloromethylated resins (Merrifield resins) and ideal for the attachment of acids by esterification. Diacids can be attached with less crosslinking compared to Merrifield resins. Release of the carboxylic acid from the resin can be effected by treatment with HF, trifluoromethane sulfonic acid or hydrogenolysis. Liberation of alcohols is established by reduction with DIBAL or LiBH4. Methyl esters can be produced by transesterification with MeONa or Ti(OEt)4/methyl propionate. Carboxamides are accessible by Lewis acid catalyzed aminolysis.
Literature
L 32 Hydroxymethyl Polystyrene Resins
- Goldwasser, J. M.; Leznoff, C. C. The Solid Phase Synthesis of Monoester Monoamides and Monoester Monoalcohols from Symmetrical Diacid Chlorides. Can. J. Chem. 1978, 56 (11), 1562-1568. doi: 10.1139/v78-253.
- Burdick, D. J.; Struble, M. E.; Burnier, J. P. Solid Phase Synthesis of Peptide Para -Nitroanilides. Tetrahedron Lett. 1993, 34 (16), 2589-2592. doi: 10.1016/s0040-4039(00)77632-5.
- Barn, D. R.; Richard Morphy, J.; Rees, D. C. Synthesis of an Array of Amides by Aluminium Chloride Assisted Cleavage of Resin-Bound Esters. Tetrahedron Lett. 1996, 37 (18), 3213-3216. doi: 10.1016/0040-4039(96)00498-4.
- Schlatter, J. M.; Mazur, R. H. Hydrogenation in Solid Phase Peptide Synthesis. I. Removal of Product from the Resin. Tetrahedron Lett. 1977, 18 (33), 2851-2852. doi: 10.1016/s0040-4039(01)83091-4.
- Kurth, M. J.; Ahlberg Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Kang, R.; Nakatsu, T.; Green, C. Library-Based Lead Compound Discovery: Antioxidants by an Analogous Synthesis/Deconvolutive Assay Strategy. J. Org. Chem. 1994, 59 (20), 5862-5864. doi: 10.1021/jo00099a008.
- Stewart J. M., Young J. D., Attachment of Boc-amino acids to hydroxymethyl resin in Solid Phase Peptide Synthesis, 2nd Ed., Rockford, Illinois, Pierce Chemical Company, 1984, 72.
- Tietze, L. F.; Steinmetz, A. Stereoselective Solid-Phase Synthesis of Cyclopentane and Cyclohexane Derivatives by Two-Component Domino Reactions: Generation of Combinatorial Libraries. Angew. Chem. Int. Ed. Engl. 1996, 35 (6), 651-652. doi: 10.1002/anie.199606511.
- Frenette, R.; Friesen, R. W. Biaryl Synthesis via Suzuki Coupling on a Solid Support. Tetrahedron Lett. 1994, 35 (49), 9177-9180. doi: 10.1016/0040-4039(94)88458-7.
- Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Solid Phase Synthesis of Hydantoins Using a Carbamate Linker and a Novel Cyclization / Cleavage Step. Tetrahedron Lett. 1996, 37 (7), 937-940. doi: 10.1016/0040-4039(95)02395-x.