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JandaJels™ are novel insoluble supports that contain a flexible tetrahyrdofuran-derived cross-linker (figure 1).
Figure 1
When performing SPOS, this novel structure offers many advantages over other commercially available polystyrene resins, including:1
- Interior that is more "organic solvent-like" than that of Divinylbenzene cross-linked resins.
- Increased swelling/solvation characteristics in common solvents used in SPOS.
- Increased site accessibility and thus resin functionality.
- Increased homogeneity.
These resins have been utilized in a wide range of applications, from a recyclable polymer-supported catalyst2, to the synthesis of phthalide3 and tertiary amine4
libraries. Further applications, are currently being investigated.
Superior Swelling characteristics of JandaJels™
Left: Merrifield-1% DVB Right: JandaJel-Cl
Volume of Swollen Resin (mL/g)
| Resin-Cross-linking |
Loading (mmol/g) |
Dioxane |
THF |
DMF |
Benzene |
CH2Cl2 |
| JandaJel-Cl-2% |
1.0 |
11.4 |
11.6 |
9.0 |
10.8 |
10.8 |
| PS/DVB-Cl-2% |
1.0 |
5.0 |
5.0 |
4.0 |
5.4 |
5.4 |
| PS/DVB-Cl-1% |
1.0 |
6.0 |
6.4 |
4.8 |
6.6 |
6.0 |
| JandaJel-OH-2% |
0.9 |
10.0 |
9.4 |
7.8 |
8.4 |
10.2 |
| PS/DVB-OH-1% |
1.1 |
6.8 |
7.0 |
5.6 |
4.8 |
7.6 |
| JandaJel-NH2-2% |
1.3 |
17.6 |
12.0 |
14.0 |
12.0 |
11.8 |
| PS/DVB-NH2-2% |
1.1 |
9.4 |
8.0 |
5.2 |
8.2 |
7.4 |
| JandaJel-Wang-2% |
0.9 |
11.4 |
12.0 |
10.0 |
9.8 |
11.4 |
| PS/DVB-Wang-2% |
0.9 |
6.2 |
6.6 |
4.4 |
5.0 |
5.4 |
Volumes were measured in syringes equipped with a sintered frit after equilibrating for 1h. The JandaJelsTM did exhibit modest swelling in ethyl ether and 1:1 THF:water. Water, acetonitrile, and ethanol were also examined, but no significant swelling was observed. All resins had dry volumes of approximately 1.5 mL/g
Reference: Toy, P.H. et. Al J. Comb. Chem., submitted for publication, 2000.
PRODUCT LIST
For applications of JandaJelsTM resins in solid-phase organic synthesis, see:
- Toy, P.H.; Janda, K.D. Tetrahedron Lett. 1999, 40, 6329.
- Toy, P.H. et al. J. Comb. Chem., submitted for publication , 2000.
- Reger, T.S.; Janda, K.D. J. Am. Chem. Soc., 2000, 122, 6929.
- Garibay, P., et al. Synlett, 1999, 9, 1438
- Toy, P.H., et al. Org. Lett., 2000, 2, 2205.
For additional information or application data on the JandaJelsTM
and JandaJelsTM resins, or any other resins for SPOS, please
contact our Technical Services Department.
JandaJelsTM is a trademark of Sigma-Aldrich Co.
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