122291-76-3Relevant academic research and scientific papers
A scalable approach to obtaining orthogonally protected β-d-idopyranosides
Hevey, Rachel,Morland, Alizee,Ling, Chang-Chun
experimental part, p. 6760 - 6772 (2012/09/25)
A practical method to obtain orthogonally protected d-idopyranose from d-galactose has been developed, which is the first method to enable synthesis of the challenging β-d-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared d-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various β-idopyranose-containing oligosaccharide targets to further probe their biological functions.
Improvements in the regioselectivity of alkylation reactions of stannylene acetals
Qin, Huiping,Grindley, T. Bruce
, p. 95 - 108 (2007/10/03)
The regioselectivity of benzylation of stannylene acetals of trans-diols on pyranose rings is improved by performing the reaction in benzyl bromide, for instance, for methyl 4,6-O-benzylidene-2,3-O-dibutylstannylene-α-D-glucopyranoside, the ratio of 2-O-b
Preparation and calculated conformations of the 2'-, 3'-, 4'-, and 6'-deoxy, 3'-O-methyl, 4'-epi, and 4'- and 6'-deoxy-fluoro derivatives of methyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (methyl beta-D-galabioside).
Kihlberg,Frejd,Jansson,Kitzing,Magnusson
, p. 171 - 190 (2007/10/02)
The glycosyl chlorides of the 3-O-methyl (6) and 4-deoxy-4-fluoro (8) O-benzylated derivatives of D-galactopyranose and 2,3,4,6-tetra-O-benzyl-D-glucopyranose were condensed with methyl 2,3,6-tri-O-benzoyl-beta-D-galactopyranoside to give, after deprotect
