Efficient selective deacetylation of complex oligosaccharides using the neutral organotin catalyst [tBu2SnOH(Cl)]2

Minghong Ni; Marco Guerrini; Annamaria Naggi; Maurice Petitou

doi:10.1016/j.carres.2020.108172

Efficient selective deacetylation of complex oligosaccharides using the neutral organotin catalyst [tBu₂SnOH(Cl)]₂

Carbohydr Res. 2020 Dec:498:108172. doi: 10.1016/j.carres.2020.108172. Epub 2020 Oct 7.

Authors

Minghong Ni¹, Marco Guerrini², Annamaria Naggi³, Maurice Petitou⁴

Affiliations

¹ Istituto di Ricerche Chimiche e Biochimiche G. Ronzoni, Via G. Colombo, 81, 20133, Milan, Italy. Electronic address: niminghong@ronzoni.it.
² Istituto di Ricerche Chimiche e Biochimiche G. Ronzoni, Via G. Colombo, 81, 20133, Milan, Italy. Electronic address: guerrini@ronzoni.it.
³ Istituto di Ricerche Chimiche e Biochimiche G. Ronzoni, Via G. Colombo, 81, 20133, Milan, Italy. Electronic address: naggi@ronzoni.it.
⁴ Istituto di Ricerche Chimiche e Biochimiche G. Ronzoni, Via G. Colombo, 81, 20133, Milan, Italy. Electronic address: petitou.ronzoni@orange.fr.

PMID: 33099244
DOI: 10.1016/j.carres.2020.108172

Abstract

Tetra-tert-butyl-3-chloro-1-hydroxydistannoxane has been found to selectively cleave with high efficiency primary acetates on complex oligosaccharides containing esterified l-iduronic acid and bearing an anomeric acetate. This tin based catalyst was found much more effective than magnesium methoxide to carry out selective deacetylation.

Keywords: Selective deacetylation; Tetra-tert-butyl-3-chloro-1-hydroxydistannoxane.

MeSH terms

Acetylation
Catalysis
Esterification
Iduronic Acid / chemistry
Oligosaccharides / chemistry*
Organotin Compounds / chemistry*

Substances

Oligosaccharides
Organotin Compounds
Iduronic Acid