Advanced Technology And Industrial Co., Ltd
Catalogue - Novelties
Solid supported chemistry

 

Solid Phase Synthesis

The use of polymer supports in organic synthesis is becoming well established as demonstrated by the massive increase in the number of publications referring to it. The key reported advantages for solid-phase synthesis being faster and simplified procedures for the generation of a large number of compounds (use of automation/ ease of purification of intermediates and products/ use of excess starting material). At Acros Organics, we understand that for a solid phase synthesis procedure to fulfill its advantageous promises, it is crucial to select the correct resin matrix and linker(s) for the reaction under consideration.

Selection
Most chemistry using solid-supported synthesis reported today uses polystyrene cross-linked with 1-2% divinyl benzene (DVB) as the resin matrix. Such resins are stable and exhibit high compatibility and good swelling characteristics with a wide range of non polar solvents; however, they fail when polar solvents are required and distancing of the reaction sites from the hydrophobic PS-DVB resin core becomes necessary. For such reactions, TentaGel®, a polystyrene/divinylbenzene - poly (ethylene glycol) graft copolymer that swells in a wide variety of polar and non-polar solvents is highly popular.

Linkers provide attachment sites for different functional groups onto the resin and their proper choice is crucial for a solid phase synthesis to be successful. Access to a wide variety of linkers is key to allow for flexibility in the design of polymer-supported chemical reactions.

Acros Organics Offer
A selection of polystyrene and TentaGel® resins for solid phase synthesis with a broad variety of linker groups and narrow-range loading capacities has been recently introduced to our stock. This selection is presented in this publication with a sampling of references to the chemistry of some of its entries. The resins are offered to customers with our assurance of accurate, consistent, and reproducible specifications at highly competitive prices. The introduction of additional resins for synthesis as well as solid-supported scavengers and reagents is underway.

Developments within this field are fast and we are working on keeping up the pace to meet our customers’ needs. Please check our website or contact your nearest Acros Organics distributor for additional entries or bulk inquiries.

 

Solution Phase Synthesis

Solution phase synthesis, where a reactive, functional group specific scavenger, a reagent, a ligand, or catalyst is attached to a polymer support, has been a fast growing area of synthesis.

This methodology takes advantage of new developments within the field of solid phase synthesis and adapts them to the existing vast repertoire of chemical reactions. Excellent publications detailing the utility, limitations, and current status of solution phase chemistry research are available.(i)

A wide range of resins for solution-phase synthesis have been introduced to Acros Organics to respond to the needs of the organic chemist adopting solution-phase strategies in his synthesis.

(i) Carmen M. Baldino; J. Comb. Chem. 2000; 2 (2), 89 -103.

 

POLYSTYRENE BASED RESINS
Scavengers of Nucleophiles and Bases
Name Reference
3-Benzyloxybenzaldehyde resin
Electrophilic scavenger resin
1% DVB; 100-200 mesh; 0.7 mmol/g
s
Sulfonyl chloride polystyrene resin.
Merrifield-type resin with an electron-rich arenesulfonyl linker.
Useful as a scavenger for alcohols. Also as a traceless solid support for aryl compounds.
1% DVB; 100-200 mesh; 1-2 mmol/g
35835
 
POLYSTYRENE BASED RESINS
Scavengers of Electrophiles and Acids
Name Reference
Diisopropylaminomethyl polystyrene resin
Scavenger resin for acids. Support for the synthesis of amides.
1% DVB; 100-200 mesh; 2-3.7 mmol/g
Couti, P. et al., Tetrahedon Lett. 1997; 38; 2915.
35840
S-(Methyl)thiomethyl polystyrene resin
Scavenger for oxidizing agents and carbocations
1% DVB; 100-200 mesh; 0.5-1.3 mmol/g
35839
Morpholinomethyl polystyrene resin
Scavenger resin for acids
1% DVB; 100-200 mesh; 2-3.5 mmol/g
Cresswell, M. W. et al. Tetrahedron 1998; 34; 3983.
35837
Piperidinomethyl polystyrene resin
Scavenger resin for acids.
1% DVB; 100-200 mesh; 2.0-3.0 mmol/g
Booth, R. J. and Hodge, J. C.; J. Am. Chem. Soc. 1997; 119; 4882.
35834
Tris(2-aminoethyl) amine resin
Popular scavenger resin for the removal of electrophiles such as alkyl halides, acid chlorides and isocyanates.
1% DVB; 100-200 mesh; 0.6-1.0 mmol/g
Cresswell, M. W. et al. Tetrahedron 1998; 34; 3983. Booth, R. J. and Hodge, J. C.; J. Am. Chem. Soc. 1997; 119; 4882.
35838
 
POLYSTYRENE BASED RESINS
Reagents and Ligands
Name Reference
Glycerol resin
Used as a protecting group for carbonyl compounds.
1% DVB; 100-200 mesh; 0.6-1 mmol/g
35830
Poly-DMAP resin
Used as a polymer-supported base and as an acid scavenger.
Also as a ligand for the generation of polymer-supported Rh hydrogenation catalyst.
1% DVB; 100-200 mesh; 0.9-2 mmol/g
35836
Polystyrene [CH2PPh3]+CI-
Polymer-bound Wittig reagent.
Also useful as a ligand for the generation of polymer-supported catalysts for Suzuki and hyrogenation reactions.
1% DVB; 100-200 mesh; 0.7-1.3 mmol/g
35832
Triphenylphosphine resin
Polymer-supported analogue of triphenylphosphine.
Versatile immobilized reagent for Wittig Mitsunobu & deoxygenation reactions.
Also used as a scavenger for alkyl halides and palladium.
1% DVB; 100-200 mesh; 1-1.5 mmol/g
Hughes, I.; Tetrahedron Lett.; 1996; 37; 7596.
35833
 
SILICA BASED RESINS
Name Reference
Silicagel, functionalised, Amino-3
for the scavenging of acids, acid chlorides, anhydrides, aldehydes, isocyanates and chloroformates
~1.4 mmol/g
Tetrahedron Lett. 2000; 41; 3573-3576.
36018
Silicagel, functionalised,Chloride-3
Merrifield type resin that can be used in solid phase synthesis
~1.5 mmol/g
36019
Silicagel, functionalised, Diol-3
For the scavenging or protection of aldehydes and ketones.
~1.1 mmol/g
36017
Silicagel, functionalised, Pentafluorophenyl-3
Used in taxol analysis and in solid-phase extraction of fluorous phases
~1 mmol/g
36021
Silicagel, functionalised, Piperidino-3
De-blocking\scavenging of Boc and Fmoc protecting groups
~2 mmol/g
J. Org. Chem. 1983; 48(5); 666.
36024
Silicagel, functionalised, Sulfonic Acid-2Ar
Strong supported acid used as an cation exchanger.
Can be used as a scavenger to remove amines from solution
~1 mmol/g
36022
Silicagel, functionalised, Tridecafluoro-2
Used in solid-phase extraction of fluorous phases
~1 mmol/g
Curran, D. P. and Luo, Z. J. Am. Chem. Soc.1999; 121; 9069.
36020
Silicagel, functionalised, trimethylamino chloride-3
Used in ion-exchange chromatography and in specific application needing anion immobilization
~1.2 mmol/g
36023


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