Reaction #1121722

ord-09dcc252cd764bf39ecf78c9fde11957

Reaction equation

C[C@@H]1OC(=O)[C@H](C)OC1=O
L-lactide
C=C(C)C(=O)OCCO
2-hydroxyethyl methacrylate
C=C(C)C(=O)OCCO.CC(O)C(=O)[O-]
HEMA lactate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherwere first reacted at 110° C. for one hour in the presence of catalyst SnOct2

Procedure

Dextran-(2-hydroxyethylmethacrylate)-lactate (Dex-lactateHEMA) macromer was synthesized according to a published method (Wolthuis, et al. Polymer, 1997, 38, 6235-6242). For example, L-lactide and 2-hydroxyethyl methacrylate (HEMA) with 1:1 molar ratio were first reacted at 110° C. for one hour in the presence of catalyst SnOct2 to obtain HEMA-lactate. Secondly, N,N′-carbonyldiimidazole (CDI) was reacted with the above HEMA-lactate product at 1:1 feeding molar ratio at room temperature in THF for 16 h to obtain HEMA-lactateCI. Finally, a calculated amount of dextran was reacted with HEMA-lactateCI (HEMAlactateCI:glucopyranose=7:1 molar ratio) in the presence of catalyst 4-(N,N-dimethylamino) pyridine (DMAP) in dimethyl sulfoxide (DMSO) at room temperature for four days to obtain the Dex-lactateHEMA macromer. The average length of lactate spacer (DPav) is equal to 3, and degree of substitute (DS; amount of methacrylate groups per 100 dextran glucopyranose residues) is equal to 4.6.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08545830B2uspto-grants-2013_10