Iodine promoted glycosylation with glycosyl iodides: α-glycoside synthesis

Renate M. van Well; K. P. Ravindranathan Kartha; Robert A. Field

doi:10.1081/CAR-200067028

Iodine promoted glycosylation with glycosyl iodides: α-glycoside synthesis

Renate M. van Well, K. P. Ravindranathan Kartha, Robert A. Field

School of Chemistry, Pharmacy and Pharmacology

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

49 Citations (Scopus)

Abstract

Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave α-glucoside selectively. Use of less reactive acceptors led to the formation of α/β-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded β-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only α-linked products in high yield in most cases.

Original language	English
Pages (from-to)	463-474
Number of pages	12
Journal	Journal of Carbohydrate Chemistry
Volume	24
Issue number	4-6
Early online date	16 Aug 2005
DOIs	https://doi.org/10.1081/CAR-200067028
Publication status	Published - 2005

Keywords

α-glycosylation
Glycosyl iodine
Glycosylated amino acids
Iodine

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10.1081/CAR-200067028

Cite this

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title = "Iodine promoted glycosylation with glycosyl iodides: α-glycoside synthesis",

abstract = "Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave α-glucoside selectively. Use of less reactive acceptors led to the formation of α/β-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded β-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only α-linked products in high yield in most cases.",

keywords = "α-glycosylation, Glycosyl iodine, Glycosylated amino acids, Iodine",

author = "{van Well}, {Renate M.} and Kartha, {K. P. Ravindranathan} and Field, {Robert A.}",

note = "Funding Information: This work was supported by an EU Marie Curie Intra-European Fellowship (to R. v W) and by the Weston Foundation. We thank the UK EPSRC Mass Spectrometry Service Centre, Swansea, for invaluable support.",

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AU - van Well, Renate M.

AU - Kartha, K. P. Ravindranathan

AU - Field, Robert A.

N1 - Funding Information: This work was supported by an EU Marie Curie Intra-European Fellowship (to R. v W) and by the Weston Foundation. We thank the UK EPSRC Mass Spectrometry Service Centre, Swansea, for invaluable support.

PY - 2005

Y1 - 2005

N2 - Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave α-glucoside selectively. Use of less reactive acceptors led to the formation of α/β-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded β-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only α-linked products in high yield in most cases.

AB - Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave α-glucoside selectively. Use of less reactive acceptors led to the formation of α/β-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded β-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only α-linked products in high yield in most cases.

KW - α-glycosylation

KW - Glycosyl iodine

KW - Glycosylated amino acids

KW - Iodine

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M3 - Article

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VL - 24

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EP - 474

JO - Journal of Carbohydrate Chemistry

JF - Journal of Carbohydrate Chemistry

SN - 0732-8303

IS - 4-6

ER -

Iodine promoted glycosylation with glycosyl iodides: α-glycoside synthesis

Abstract

Keywords

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