Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry XII. Tuning promoter reactivity for thioglycoside activation

P. Cura; M. Aloui; K. P. Ravindranathan Kartha; R. A. Field

Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry XII. Tuning promoter reactivity for thioglycoside activation

P. Cura, M. Aloui, K. P. Ravindranathan Kartha, R. A. Field

School of Chemistry, Pharmacy and Pharmacology

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

19 Citations (Scopus)

Abstract

The reactivity of O-benzylated 1-thio-β-D-galactopyranosides in iodine-promoted methanolysis reactions was shown to correlate with aglycone structure, as expected (R = p.NO₂Ph < Ph < Bn < p.MeOPh < Me). The rate of methanolysis could be altered substantially through appropriate choice of promoter (ICl > IBr ~ I₂+DDQ > I₂), with even the unreactive nitrophenyl thioglycoside undergoing complete reaction in less than 2 minutes in acetonitrile in the presence of ICl.

Original language	English
Pages (from-to)	1279-1280
Number of pages	2
Journal	Synlett
Issue number	9
Publication status	Published - 2000

Keywords

Glycosylation
Iodine
Thioglycosides

Cite this

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title = "Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry XII. Tuning promoter reactivity for thioglycoside activation",

abstract = "The reactivity of O-benzylated 1-thio-β-D-galactopyranosides in iodine-promoted methanolysis reactions was shown to correlate with aglycone structure, as expected (R = p.NO2Ph < Ph < Bn < p.MeOPh < Me). The rate of methanolysis could be altered substantially through appropriate choice of promoter (ICl > IBr ~ I2+DDQ > I2), with even the unreactive nitrophenyl thioglycoside undergoing complete reaction in less than 2 minutes in acetonitrile in the presence of ICl.",

keywords = "Glycosylation, Iodine, Thioglycosides",

author = "P. Cura and M. Aloui and {Ravindranathan Kartha}, {K. P.} and Field, {R. A.}",

year = "2000",

language = "English",

pages = "1279--1280",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "9",

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TY - JOUR

T1 - Iodine and its interhalogen compounds

T2 - Versatile reagents in carbohydrate chemistry XII. Tuning promoter reactivity for thioglycoside activation

AU - Cura, P.

AU - Aloui, M.

AU - Ravindranathan Kartha, K. P.

AU - Field, R. A.

PY - 2000

Y1 - 2000

N2 - The reactivity of O-benzylated 1-thio-β-D-galactopyranosides in iodine-promoted methanolysis reactions was shown to correlate with aglycone structure, as expected (R = p.NO2Ph < Ph < Bn < p.MeOPh < Me). The rate of methanolysis could be altered substantially through appropriate choice of promoter (ICl > IBr ~ I2+DDQ > I2), with even the unreactive nitrophenyl thioglycoside undergoing complete reaction in less than 2 minutes in acetonitrile in the presence of ICl.

AB - The reactivity of O-benzylated 1-thio-β-D-galactopyranosides in iodine-promoted methanolysis reactions was shown to correlate with aglycone structure, as expected (R = p.NO2Ph < Ph < Bn < p.MeOPh < Me). The rate of methanolysis could be altered substantially through appropriate choice of promoter (ICl > IBr ~ I2+DDQ > I2), with even the unreactive nitrophenyl thioglycoside undergoing complete reaction in less than 2 minutes in acetonitrile in the presence of ICl.

KW - Glycosylation

KW - Iodine

KW - Thioglycosides

UR - http://www.scopus.com/inward/record.url?scp=0033804717&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0033804717

SP - 1279

EP - 1280

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 9

ER -

Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry XII. Tuning promoter reactivity for thioglycoside activation

Abstract

Keywords

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