74410-55-2

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 
• 86470-08-8 methyl 4,6-O-benzylidene-β-D-galactopyranoside 3-O-p-toluenesulfonate 
• 124-41-4 sodium methylate 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 66674-14-4 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 120408-72-2 Methyl 2,3-anhydro-4,6-O-(phenylmethylene)-β-D-allopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 

Downstream Products

• 3013-58-9 methyl 4,6-O-(S)-benzylidene-2,3-di-O-methyl-β-D-idopyranoside 
• 6749-00-4 methyl-[O⁴,O⁶-((R)-benzylidene)-O²-methyl-O³-(toluene-4-sulfonyl)-α-D-altropyranoside] 
• 120200-52-4 methyl-[O⁴,O⁶-((R)-benzylidene-O²,O³-dimethyl-α-D-altropyranoside] 
• 144290-78-8 methyl-[O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-O²-methyl-α-D-altropyranoside] 
• 183182-16-3 methyl 4,6-O-benzylidene-3-O-methanesulfonyl-2-O-methyl-α-D-altropyranoside 
• 183001-89-0 (3S,4R,5R)-4-Benzyloxy-5-((R)-2-hydroxy-1-methoxy-ethyl)-tetrahydro-thiophen-3-ol 
• 1214746-65-2 methyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-O-methyl-α-D-altropyranoside 
• 183001-83-4 Benzoic acid (2S,3R,4R,5S,6S)-2-acetylsulfanylmethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester 
• 183001-82-3 Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester 
• 183001-85-6 methyl 4-O-benzyl-2-O-methyl-3,6-thioanhydro-α-D-mannopyranoside 
• 183001-93-6 (R)-((2S,3R,4S)-3-Benzyloxy-4-hydroxy-tetrahydro-thiophen-2-yl)-methoxy-acetaldehyde 
• 88390-62-9 methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-arabinohexopyranosid-3-ulose 

Relevant academic research and scientific papers

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.

New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

New d-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene).