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JandaJels™

JandaJels™ are novel insoluble supports that contain a flexible tetrahyrdofuran-derived cross-linker (figure 1).


<i>J</i>anda<i>J</i>el 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™
<i>J</i>anda<i>J</i>el Figure 2
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:

  1. Toy, P.H.; Janda, K.D. Tetrahedron Lett. 1999, 40, 6329.
  2. Toy, P.H. et al. J. Comb. Chem., submitted for publication , 2000.
  3. Reger, T.S.; Janda, K.D. J. Am. Chem. Soc., 2000, 122, 6929.
  4. Garibay, P., et al. Synlett, 1999, 9, 1438
  5. 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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