Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride

Ju Yuel Baek; Bo Young Lee; Rita Pal; Won Yong Lee; Kwan Soo Kim

doi:10.1016/j.tetlet.2010.09.064

Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride

Ju Yuel Baek, Bo Young Lee, Rita Pal, Won Yong Lee, Kwan Soo Kim

Department of Chemistry

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

13 Citations (Scopus)

Abstract

An efficient and direct one-pot glycosylation method using anomeric hydroxy sugars as glycosyl donors, employing 3-fluorophthalic anhydride and triflic anhydride as activating agents, has been developed. The present glycosylation utilizing 3-fluorophthalic anhydride resulted in few to no undesired self-condensed esters than the glycosylation using phthalic anhydride. Intermediates in the present glycosylation were identified by an NMR study.

Original language	English
Pages (from-to)	6250-6254
Number of pages	5
Journal	Tetrahedron Letters
Volume	51
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2010.09.064
Publication status	Published - 2010 Dec 1

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation (NRF) grant funded by the Korea government (MEST) through the Center for Bioactive Molecular Hybrids (No. R11-2003-019-00000-0 ).

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.09.064

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title = "Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride",

abstract = "An efficient and direct one-pot glycosylation method using anomeric hydroxy sugars as glycosyl donors, employing 3-fluorophthalic anhydride and triflic anhydride as activating agents, has been developed. The present glycosylation utilizing 3-fluorophthalic anhydride resulted in few to no undesired self-condensed esters than the glycosylation using phthalic anhydride. Intermediates in the present glycosylation were identified by an NMR study.",

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note = "Funding Information: This work was supported by the National Research Foundation (NRF) grant funded by the Korea government (MEST) through the Center for Bioactive Molecular Hybrids (No. R11-2003-019-00000-0 ). ",

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T1 - Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride

AU - Baek, Ju Yuel

AU - Lee, Bo Young

AU - Pal, Rita

AU - Lee, Won Yong

AU - Kim, Kwan Soo

N1 - Funding Information: This work was supported by the National Research Foundation (NRF) grant funded by the Korea government (MEST) through the Center for Bioactive Molecular Hybrids (No. R11-2003-019-00000-0 ).

PY - 2010/12/1

Y1 - 2010/12/1

N2 - An efficient and direct one-pot glycosylation method using anomeric hydroxy sugars as glycosyl donors, employing 3-fluorophthalic anhydride and triflic anhydride as activating agents, has been developed. The present glycosylation utilizing 3-fluorophthalic anhydride resulted in few to no undesired self-condensed esters than the glycosylation using phthalic anhydride. Intermediates in the present glycosylation were identified by an NMR study.

AB - An efficient and direct one-pot glycosylation method using anomeric hydroxy sugars as glycosyl donors, employing 3-fluorophthalic anhydride and triflic anhydride as activating agents, has been developed. The present glycosylation utilizing 3-fluorophthalic anhydride resulted in few to no undesired self-condensed esters than the glycosylation using phthalic anhydride. Intermediates in the present glycosylation were identified by an NMR study.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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