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Molecular Diversity

, Volume 9, Issue 4, pp 305–316 | Cite as

High-loading polyglycerol supported reagents for Mitsunobu- and acylation-reactions and other useful polyglycerol derivatives

  • Sebastian Roller
  • Haixia Zhou
  • Rainer Haag
Full-length paper

Summary

In this paper we present soluble dendritic polyglycerol (PG) supported reagents PG-DEAD, PG-PPh3, and PG-DCC as well as scavengers PG-carbonate, PG-carbazate, and PG-amine, which all have been synthesized in high overall conversions and yields using simple purification techniques. The supported reagents have been used simultaneously in Mitsunobu and acylation reactions. All polymeric reagents and scavengers can be removed by simple precipitation/filtration protocols to give chromatography-free products of high purity. In the course of the syntheses of the polymeric reagents three intermediates turned out to be precious polyglycerol derivatives: a mixed carbonate as an electrophilic derivative, polyglyceryl carbazate as a scavenger for carbonyl compounds, as well as polyglycerylamines as amino analogues of polyglycerol.

Key Words

dendrimer hyperbranched polymer polyglycerol polymeric reagent scavenger soluble polymeric support supported azodicarboxylate supported carbodiimide supported triphenylphosphine 

Abbreviations

abs

absolute

aq

aqueous

Bn

benzyl

DB

degree of branching

DCC

N,N′-dicyclohexyl carbodiimide

DCM

dichloromethane

DCU

N,N′-dicyclohexyl urea

DEAD

diethylazodicarboxylate

DMAP

N,N-dimethylaminopyridine

EDCI

N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide

EDCU

N-(3-dimethylaminopropyl)-N′-ethyl-urea

Fmoc

fluorenylmethoxycarbonyl

IR

infrared

MALDITOF

matrix assisted LASER desorption ionization time of flight

MPEG

monomethylated poly(ethylene glycol)

Mn

number–average molar mass

Ms

mesyl, methansulfonyl

NBS

N-bromosuccinimide

MWCO

molecular weight cut-off

NMR

nuclear magnetic resonance

p.a.

pro analysi

PG

polyglycerol

PS

polystyrene

ROMP

ring opening metathesis polymerization

sat

saturated

THF

tetrahydrofurane

TLC

thin layer chromatography

Ts

tosyl, p-toluenesulfonyl

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Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  1. 1.Organische ChemieUniversität DortmundDortmundGermany

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