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Esterification of polymer-supported hydroxyl groups using the Mitsunobu reaction

✍ Scribed by Viktor Krchňák; Dasha Cabel; Aleksandra Weichsel; Zuzka Flegelová

Book ID
104628731
Publisher
Springer Netherlands
Year
1995
Tongue
English
Weight
336 KB
Volume
1
Category
Article
ISSN
1573-3149

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✦ Synopsis

Resin-bound hydroxyl groups were esterified by N-protected amino acids using triphenylphosphine and diethyl azodicarboxylate (Mitsunobu reaction) in tetrahydrofuran or dimethylformamide. The typical reaction time was 1 h and the yield for different amino acids varied from 65 to 100%. No racemization was detected in model peptides.

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Treatment of equatorial cyclohexanols with Ph3P/DEAD/MsOH gives clean conversion to the axial mesylates. Subsequent reaction with NaN3 gives the equatorial azides in overall yields of 74-87%. Axial hydroxyl groups are not affected, allowing the regioselective conversion of methyl cholate into a 3ct-