Hexafluoroacetone as a protecting and activating reagent. Regioselective esterification of aspartic, malic, and thiomalic acid

Ksenia Pumpor; Elisabeth Windeisen; Jan Spengler; Fernando Albericio; Klaus Burger

doi:10.1007/s00706-004-0183-9

Hexafluoroacetone as a protecting and activating reagent. Regioselective esterification of aspartic, malic, and thiomalic acid

Ksenia Pumpor
, Elisabeth Windeisen
, Jan Spengler
, Fernando Albericio
, Klaus Burger

Leipzig University
University of Barcelona

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Hexafluoroacetone reacts with α-functionalized α,β- dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.

Original language	English
Pages (from-to)	1427-1443
Number of pages	17
Journal	Monatshefte fur Chemie
Volume	135
Issue number	11
DOIs	https://doi.org/10.1007/s00706-004-0183-9
State	Published - Nov 2004
Externally published	Yes

Keywords

Branched depsipeptides
Branched peptides
Hexafluoroacetone
Peptidomimetics
Polyester

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10.1007/s00706-004-0183-9

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abstract = "Hexafluoroacetone reacts with α-functionalized α,β- dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.",

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T1 - Hexafluoroacetone as a protecting and activating reagent. Regioselective esterification of aspartic, malic, and thiomalic acid

AU - Pumpor, Ksenia

AU - Windeisen, Elisabeth

AU - Spengler, Jan

AU - Albericio, Fernando

AU - Burger, Klaus

PY - 2004/11

Y1 - 2004/11

N2 - Hexafluoroacetone reacts with α-functionalized α,β- dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.

AB - Hexafluoroacetone reacts with α-functionalized α,β- dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.

KW - Branched depsipeptides

KW - Branched peptides

KW - Hexafluoroacetone

KW - Peptidomimetics

KW - Polyester

UR - https://www.scopus.com/pages/publications/11144316824

U2 - 10.1007/s00706-004-0183-9

DO - 10.1007/s00706-004-0183-9

M3 - Artículo

AN - SCOPUS:11144316824

SN - 0026-9247

VL - 135

SP - 1427

EP - 1443

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 11

ER -

Hexafluoroacetone as a protecting and activating reagent. Regioselective esterification of aspartic, malic, and thiomalic acid

Abstract

Keywords

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