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  • Iodine monochloride/silver trifluoromethanesulfonate (ICI/AgOTf) as a convenient promoter system for O-glycoside synthesis.

Iodine monochloride/silver trifluoromethanesulfonate (ICI/AgOTf) as a convenient promoter system for O-glycoside synthesis.

Organic letters (2001-03-27)
T Ercegovic, A Meijer, G Magnusson, U Ellervik
ABSTRACT

The novel promoter system iodine monochloride/silver trifluoromethanesulfonate (ICl/AgOTf) was evaluated with various thioglycoside donors and saccharide acceptors, and O-glycosides were obtained in 46-82% yield. Several practical advantages of the ICl/AgOTf system over known promoter systems were observed, such as convenient handling of the reagents and absence of byproducts related to N-succinimide.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Iodine monochloride, 99.998% trace metals basis
Sigma-Aldrich
Iodine monochloride solution, 1 M in acetic acid
Sigma-Aldrich
Iodine monochloride solution, 1.0 M in methylene chloride
Sigma-Aldrich
Silver trifluoromethanesulfonate, purum, ≥98.0% (Ag)
Sigma-Aldrich
Iodine monochloride, reagent grade, ≥95%
Sigma-Aldrich
Iodine monochloride, ACS reagent, 1.10±0.1 I/Cl ratio basis