Use of polystyrene-supported DBU in the synthesis and α-selective glycosylation study of the unstable schmidt donor of L-kedarosamine

Isao Ohashi; Martin James Lear; Fumihiko Yoshimura; Masahiro Hirama

doi:10.1021/ol036353v

Use of polystyrene-supported DBU in the synthesis and α-selective glycosylation study of the unstable schmidt donor of L-kedarosamine

Isao Ohashi, Martin James Lear, Fumihiko Yoshimura, Masahiro Hirama

SCI - Chemistry

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

18 Citations (Scopus)

Abstract

In the α-glycosylation study of the unusual, 2-deoxy amino sugar of kedarcidin, polystyrene-supported DBU (PDBU) was found to be invaluable to the clean preparation of the highly labile Schmidt donor of L-kedarosamine. By further recognition that the C4-alcohol should be left free for favorable acceptor reactivity, we could for the first time successfully assemble the C13-O-α-glycoside of the ansamacrolide substructure of the kedarcidin chromophore.

Original language	English
Pages (from-to)	719-722
Number of pages	4
Journal	Organic letters
Volume	6
Issue number	5
DOIs	https://doi.org/10.1021/ol036353v
Publication status	Published - 2004 Mar 4

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "In the α-glycosylation study of the unusual, 2-deoxy amino sugar of kedarcidin, polystyrene-supported DBU (PDBU) was found to be invaluable to the clean preparation of the highly labile Schmidt donor of L-kedarosamine. By further recognition that the C4-alcohol should be left free for favorable acceptor reactivity, we could for the first time successfully assemble the C13-O-α-glycoside of the ansamacrolide substructure of the kedarcidin chromophore.",

author = "Isao Ohashi and Lear, {Martin James} and Fumihiko Yoshimura and Masahiro Hirama",

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T1 - Use of polystyrene-supported DBU in the synthesis and α-selective glycosylation study of the unstable schmidt donor of L-kedarosamine

AU - Ohashi, Isao

AU - Lear, Martin James

AU - Yoshimura, Fumihiko

AU - Hirama, Masahiro

PY - 2004/3/4

Y1 - 2004/3/4

N2 - In the α-glycosylation study of the unusual, 2-deoxy amino sugar of kedarcidin, polystyrene-supported DBU (PDBU) was found to be invaluable to the clean preparation of the highly labile Schmidt donor of L-kedarosamine. By further recognition that the C4-alcohol should be left free for favorable acceptor reactivity, we could for the first time successfully assemble the C13-O-α-glycoside of the ansamacrolide substructure of the kedarcidin chromophore.

AB - In the α-glycosylation study of the unusual, 2-deoxy amino sugar of kedarcidin, polystyrene-supported DBU (PDBU) was found to be invaluable to the clean preparation of the highly labile Schmidt donor of L-kedarosamine. By further recognition that the C4-alcohol should be left free for favorable acceptor reactivity, we could for the first time successfully assemble the C13-O-α-glycoside of the ansamacrolide substructure of the kedarcidin chromophore.

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ER -

Use of polystyrene-supported DBU in the synthesis and α-selective glycosylation study of the unstable schmidt donor of L-kedarosamine

Abstract

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