21056-53-1Relevant articles and documents
Tin-mediated regioselective acylation of unprotected sugars on solid phase
Peri,Cipolla,Nicotra
, p. 8587 - 8590 (2000)
Methyl α-D-glucopyranoside, methyl α-D-mannopyranoside and methyl β-D-galactopyranoside bound on O-6 to a copolystyrene-DVB resin through a trityl ether linker, have been regioselectively acylated with benzoyl chloride after treatment with Bu2S
Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides
Rasool, Javeed Ur,Kumar, Atul,Ali, Asif,Ahmed, Qazi Naveed
, p. 338 - 347 (2021/01/29)
A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is
Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups
Rocheleau, Sylvain,Pottel, Joshua,Huski?, Igor,Moitessier, Nicolas
, p. 646 - 656 (2017/02/05)
The regioselective functionalization of monosaccharides is notoriously achieved using metal catalysis, lengthy synthetic strategies requiring protection/deprotection, various enzymes, or other methods that target cis-diols (and thus cannot be used with glucopyranose derivatives), In this paper, we report a new method using selected boronic acids as temporary protecting groups, and describe its application to the regioselective functionalization of methyl α-d-glucopyranoside, the most difficult monosaccharide to functionalize regioselectively. Generally, reactions of glucopyranosides may lead to a plethora of mono- and polyfunctionalized derivatives, yet our method gave the 3-O-acetylated, 2-O-benzoylated, and 2-O-pivaloylated derivatives of methyl α-d-glucopyranoside as major products. We focused on the use of recyclable and green temporary protecting groups (in a one-pot reaction) and on the modulation of the intramolecular hydrogen-bonding network using selected arylboronic acids. A complete scalable procedure leading to a single regioisomer from unprotected methyl α-d-glucopyranoside is presented.
Magnesium ion enhances lanthanum-promoted monobenzoylation of a monosaccharide in water
Dhiman, Raj S.,Kluger, Ronald
supporting information; experimental part, p. 2006 - 2008 (2010/07/03)
Magnesium ion combines selectively with the methyl phosphate by-product in the lanthanum-promoted biomimetic reaction of benzoyl methyl phosphate with monosaccharides.