Fluorous "racemic" mixture synthesis: Polysaccharide-based chiral columns for simultaneous demix and enantioseparation of racemic fluorous tagged compounds

Takayuki Tonoi; Wei Zhang; Dennis P. Curran; Koichi Mikami

doi:10.1002/chir.20487

Fluorous "racemic" mixture synthesis: Polysaccharide-based chiral columns for simultaneous demix and enantioseparation of racemic fluorous tagged compounds

Takayuki Tonoi
, Wei Zhang
, Dennis P. Curran
, Koichi Mikami

Tokyo Medical and Dental University
Fluorous Technologies, Inc
University of Pittsburgh

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

Abstract

The proof of concept experiments of fluorous "racemic" mixture synthesis (FRMS) is shown using polysaccharide-based chiral stationary phases. The mixture of racemic O-benzoylmandelate derivatives bearing different lengths of fluorous cleavable tags undergoes sequential reactions to provide individual derivatives as well as their enantiomers resolved on polysaccharide-based chiral HPLC columns (DAICEL CHIRALCEL® and CHIRALPAK® series).

Original language	English
Pages (from-to)	597-603
Number of pages	7
Journal	Chirality
Volume	20
Issue number	3-4
DOIs	https://doi.org/10.1002/chir.20487
State	Published - 2008
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
Analytical Chemistry
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

Keywords

Chiral HPLC column
Combinatorial chemistry
Enantioseparation
Fluorous racemic mixture synthesis (FRMS)
Fluorous tag

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10.1002/chir.20487

Cite this

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abstract = "The proof of concept experiments of fluorous {"}racemic{"} mixture synthesis (FRMS) is shown using polysaccharide-based chiral stationary phases. The mixture of racemic O-benzoylmandelate derivatives bearing different lengths of fluorous cleavable tags undergoes sequential reactions to provide individual derivatives as well as their enantiomers resolved on polysaccharide-based chiral HPLC columns (DAICEL CHIRALCEL{\textregistered} and CHIRALPAK{\textregistered} series).",

keywords = "Chiral HPLC column, Combinatorial chemistry, Enantioseparation, Fluorous racemic mixture synthesis (FRMS), Fluorous tag",

author = "Takayuki Tonoi and Wei Zhang and Curran, \{Dennis P.\} and Koichi Mikami",

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doi = "10.1002/chir.20487",

language = "English",

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journal = "Chirality",

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AU - Tonoi, Takayuki

AU - Zhang, Wei

AU - Curran, Dennis P.

AU - Mikami, Koichi

PY - 2008

Y1 - 2008

N2 - The proof of concept experiments of fluorous "racemic" mixture synthesis (FRMS) is shown using polysaccharide-based chiral stationary phases. The mixture of racemic O-benzoylmandelate derivatives bearing different lengths of fluorous cleavable tags undergoes sequential reactions to provide individual derivatives as well as their enantiomers resolved on polysaccharide-based chiral HPLC columns (DAICEL CHIRALCEL® and CHIRALPAK® series).

AB - The proof of concept experiments of fluorous "racemic" mixture synthesis (FRMS) is shown using polysaccharide-based chiral stationary phases. The mixture of racemic O-benzoylmandelate derivatives bearing different lengths of fluorous cleavable tags undergoes sequential reactions to provide individual derivatives as well as their enantiomers resolved on polysaccharide-based chiral HPLC columns (DAICEL CHIRALCEL® and CHIRALPAK® series).

KW - Chiral HPLC column

KW - Combinatorial chemistry

KW - Enantioseparation

KW - Fluorous racemic mixture synthesis (FRMS)

KW - Fluorous tag

UR - https://www.scopus.com/pages/publications/39749129747

UR - https://www.scopus.com/pages/publications/39749129747#tab=citedBy

U2 - 10.1002/chir.20487

DO - 10.1002/chir.20487

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SN - 0899-0042

VL - 20

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EP - 603

JO - Chirality

JF - Chirality

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ER -

Fluorous "racemic" mixture synthesis: Polysaccharide-based chiral columns for simultaneous demix and enantioseparation of racemic fluorous tagged compounds

Abstract

ASJC Scopus Subject Areas

Keywords

Access to Document

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