35780-85-9

Upstream product

• 2880-96-8 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-gulopyranoside 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 120408-72-2 Methyl 2,3-anhydro-4,6-O-(phenylmethylene)-β-D-allopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 34698-05-0 methyl 2-O-methyl-β-D-galactopyranoside 
• 157068-70-7 methyl 2-O-methyl-3,4-O-(methylethylidene)-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 143520-33-6 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-2-O-methyl-β-D-galactopyranoside 
• 104530-15-6 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 
• 124-41-4 sodium methylate 
• 86470-08-8 methyl 4,6-O-benzylidene-β-D-galactopyranoside 3-O-p-toluenesulfonate 

Downstream Products

• 3013-58-9 methyl 4,6-O-(S)-benzylidene-2,3-di-O-methyl-β-D-idopyranoside 
• 157068-63-8 methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside 
• 1053621-92-3 2,2-Dimethyl-propionic acid (2S,3R,4S,6S)-2-((2R,3R,4R,5R,6R)-4-amino-2-benzyloxymethyl-5,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-benzyloxymethyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester 
• 157068-64-9 methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside 
• 157068-65-0 methyl 3-amino-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-3-N-<(trichloroacetamido)carbonyl>-β-D-gulopyranoside 

Relevant academic research and scientific papers

An Ezomycin Model Glycosylation

A model glycosylation reaction for application to the synthesis of the ezomycin class of antibiotics is described.The ezoaminuroic thioglycoside donor 13, with a reduced and protected C-6 position and trifluoroacetamide at C-3, was prepared from the Cerny epoxide 7 by a nine-step procedure.The model D-gulo-pyranoside acceptor 20, which closely resembles an actual acceptor in the vicinity of the reacting axial hydroxyl, was synthesized from methyl β-D-galactopyranoside 14.Glycosylation with N-iodosuccinimide/triflic acid as promoter gave the disaccharide 21 in 90percent yield.

A scalable approach to obtaining orthogonally protected β-d-idopyranosides

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.