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 journalArticle

26 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 languageEnglish
Pages (from-to)4167-4170
Number of pages4
JournalOrganic Letters
Volume10
Issue number19
DOIs
Publication statusPublished - Dec 1 2008
Externally publishedYes

Fingerprint

Stereoselectivity
Ireland
Galactose
Hydroxyl Radical
Thermal effects
analogs
deoxygenation
galactose
synthesis
temperature effects
Temperature
products

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of CH2-linked α(2,3)sialylgalactose analogue : On the stereoselectivity of the key Ireland-Claisen rearrangement. / Watanabe, Toru; Hirai, Go; Kato, Marie; Hashizume, Daisuke; Miyagi, Taeko; Sodeoka, Mikiko.

In: Organic Letters, Vol. 10, No. 19, 01.12.2008, p. 4167-4170.

Research output: Contribution to journalArticle

Watanabe, Toru ; Hirai, Go ; Kato, Marie ; Hashizume, Daisuke ; Miyagi, Taeko ; Sodeoka, Mikiko. / Synthesis of CH2-linked α(2,3)sialylgalactose analogue : On the stereoselectivity of the key Ireland-Claisen rearrangement. In: Organic Letters. 2008 ; Vol. 10, No. 19. pp. 4167-4170.
@article{73f29dbd4050476aa389a352daa22a9d,
title = "Synthesis of CH2-linked α(2,3)sialylgalactose analogue: On the stereoselectivity of the key Ireland-Claisen rearrangement",
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.",
author = "Toru Watanabe and Go Hirai and Marie Kato and Daisuke Hashizume and Taeko Miyagi and Mikiko Sodeoka",
year = "2008",
month = "12",
day = "1",
doi = "10.1021/ol801519j",
language = "English",
volume = "10",
pages = "4167--4170",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "19",

}

TY - JOUR

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 - 2008/12/1

Y1 - 2008/12/1

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.

UR - http://www.scopus.com/inward/record.url?scp=55449115386&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=55449115386&partnerID=8YFLogxK

U2 - 10.1021/ol801519j

DO - 10.1021/ol801519j

M3 - Article

VL - 10

SP - 4167

EP - 4170

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 19

ER -