201533-27-9

Upstream product

• 78153-79-4 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl fluoride 
• 70639-89-3 methyl 3-(trimethylsilylmethyl)-3-butenoate 
• 143615-35-4 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl fluoride 

Downstream Products

• 219527-70-5 3-Methyl-4-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester 
• 201533-32-6 ((3aR,5R,6S,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran-2-yl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of α-C-D-gluco- and D-galactopyranosyl glycosides from an isoprenoid synthon

Addition of the allylsilane Me3SiCH2C:CH2CH2CO2Me to D-gluco and D- galactopyranosyl derivatives gives in good yields α-C-glycopyranosides which are easily converted into glycosylated β-keto esters, butenolide and dihydropyrone.

Stereoselective synthesis of α-C-glycopyranosyl isoprenoid compounds

Addition of the allylsilane Me3SiCH2C:CH2CH2CO2Me (3) to D-gluco and D-galactopyranosyl derivatives gives in good yields 3-(α-C-glycopyranosylmethyl)-but-3-enoates which can undergo oxidation to β-ketoesters, electrophile-promoted cyclizations or double bond migration.