Observations on iodine-promoted β-mannosylation

Steven J. Marsh; K. P. Ravindranathan Kartha; Robert A. Field

doi:10.1055/s-2003-40346

Observations on iodine-promoted β-mannosylation

Steven J. Marsh, K. P. Ravindranathan Kartha, Robert A. Field

School of Chemistry, Pharmacy and Pharmacology

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

22 Citations (Scopus)

Abstract

The stereoselectivity of iodine-promoted glycosylation with mannosyl sulfoxides gives rise to unexpected β-selectivity with less reactive alcohol acceptors. Less reactive accceptors also give better coupling yields. Comparison of iodine with other promoters highlights differences in reaction rates and stereoselectivities indicative of different reaction mechanisms.

Original language	English
Pages (from-to)	1376-1378
Number of pages	3
Journal	Synlett
Issue number	9 SPEC. ISS.
DOIs	https://doi.org/10.1055/s-2003-40346
Publication status	Published - 2003

Keywords

Carbohydrates
Glycosylations
Iodine
Stereoselectivity
Sulfoxides

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10.1055/s-2003-40346

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title = "Observations on iodine-promoted β-mannosylation",

abstract = "The stereoselectivity of iodine-promoted glycosylation with mannosyl sulfoxides gives rise to unexpected β-selectivity with less reactive alcohol acceptors. Less reactive accceptors also give better coupling yields. Comparison of iodine with other promoters highlights differences in reaction rates and stereoselectivities indicative of different reaction mechanisms.",

keywords = "Carbohydrates, Glycosylations, Iodine, Stereoselectivity, Sulfoxides",

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year = "2003",

doi = "10.1055/s-2003-40346",

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AU - Kartha, K. P. Ravindranathan

AU - Field, Robert A.

PY - 2003

Y1 - 2003

N2 - The stereoselectivity of iodine-promoted glycosylation with mannosyl sulfoxides gives rise to unexpected β-selectivity with less reactive alcohol acceptors. Less reactive accceptors also give better coupling yields. Comparison of iodine with other promoters highlights differences in reaction rates and stereoselectivities indicative of different reaction mechanisms.

AB - The stereoselectivity of iodine-promoted glycosylation with mannosyl sulfoxides gives rise to unexpected β-selectivity with less reactive alcohol acceptors. Less reactive accceptors also give better coupling yields. Comparison of iodine with other promoters highlights differences in reaction rates and stereoselectivities indicative of different reaction mechanisms.

KW - Carbohydrates

KW - Glycosylations

KW - Iodine

KW - Stereoselectivity

KW - Sulfoxides

UR - http://www.scopus.com/inward/record.url?scp=0038442164&partnerID=8YFLogxK

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DO - 10.1055/s-2003-40346

M3 - Article

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EP - 1378

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 9 SPEC. ISS.

ER -

Observations on iodine-promoted β-mannosylation

Abstract

Keywords

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