Synthesis of CH2-linked α(2,3)sialylgalactose analogue: On the stereoselectivity of the key Ireland-Claisen rearrangement

Toru Watanabe; Go Hirai; Marie Kato; Daisuke Hashizume; Taeko Miyagi; Mikiko Sodeoka

doi:10.1021/ol801519j

Synthesis of CH₂-linked α(2,3)sialylgalactose analogue: On the stereoselectivity of the key Ireland-Claisen rearrangement

Toru Watanabe, Go Hirai, Marie Kato, Daisuke Hashizume, Taeko Miyagi, Mikiko Sodeoka

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

31 Citations (Scopus)

Abstract

(Chemical Equation Presented) A CH₂-linked α(2,3) sialylgalactose analogue was efficiently synthesized using an Ireland-Claisen rearrangement, which was developed recently by our group for constructing a CF₂-sialoside. The reaction conditions of the rearrangement were optimized for α-stereoselective formation of the CH₂-sialoside. On the basis of the observed temperature effects, the origin of the stereoselectivity of the Ireland-Claisen rearrangement is discussed. Moreover, reconstruction of the 2α-hydroxyl group on the galactose unit of the rearrangement product was achieved by means of stereoselective dihydroxylation and deoxygenation.

Original language	English
Pages (from-to)	4167-4170
Number of pages	4
Journal	Organic letters
Volume	10
Issue number	19
DOIs	https://doi.org/10.1021/ol801519j
Publication status	Published - 2008
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol801519j

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abstract = "(Chemical Equation Presented) A CH2-linked α(2,3) sialylgalactose analogue was efficiently synthesized using an Ireland-Claisen rearrangement, which was developed recently by our group for constructing a CF2-sialoside. The reaction conditions of the rearrangement were optimized for α-stereoselective formation of the CH2-sialoside. On the basis of the observed temperature effects, the origin of the stereoselectivity of the Ireland-Claisen rearrangement is discussed. Moreover, reconstruction of the 2α-hydroxyl group on the galactose unit of the rearrangement product was achieved by means of stereoselective dihydroxylation and deoxygenation.",

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T1 - Synthesis of CH2-linked α(2,3)sialylgalactose analogue

T2 - On the stereoselectivity of the key Ireland-Claisen rearrangement

AU - Watanabe, Toru

AU - Hirai, Go

AU - Kato, Marie

AU - Hashizume, Daisuke

AU - Miyagi, Taeko

AU - Sodeoka, Mikiko

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) A CH2-linked α(2,3) sialylgalactose analogue was efficiently synthesized using an Ireland-Claisen rearrangement, which was developed recently by our group for constructing a CF2-sialoside. The reaction conditions of the rearrangement were optimized for α-stereoselective formation of the CH2-sialoside. On the basis of the observed temperature effects, the origin of the stereoselectivity of the Ireland-Claisen rearrangement is discussed. Moreover, reconstruction of the 2α-hydroxyl group on the galactose unit of the rearrangement product was achieved by means of stereoselective dihydroxylation and deoxygenation.

AB - (Chemical Equation Presented) A CH2-linked α(2,3) sialylgalactose analogue was efficiently synthesized using an Ireland-Claisen rearrangement, which was developed recently by our group for constructing a CF2-sialoside. The reaction conditions of the rearrangement were optimized for α-stereoselective formation of the CH2-sialoside. On the basis of the observed temperature effects, the origin of the stereoselectivity of the Ireland-Claisen rearrangement is discussed. Moreover, reconstruction of the 2α-hydroxyl group on the galactose unit of the rearrangement product was achieved by means of stereoselective dihydroxylation and deoxygenation.

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Synthesis of CH₂-linked α(2,3)sialylgalactose analogue: On the stereoselectivity of the key Ireland-Claisen rearrangement

Abstract

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