72523-59-2

Upstream product

• 63568-00-3 (2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile 
• 84799-67-7 hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ^1,α-acetonitrile 
• 558461-45-3 (+)-(2E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-(methoxymethoxy)-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile 
• 930117-58-1 (2E)-[(4R,5R,6S)-4,5-diacetoxy-6-{[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl]oxy}-cyclohex-2-en-1-ylidene]ethanenitrile 
• 930117-55-8 (2E)-[(4R,5S,6S)-4,5-(cyclohexylidenedioxy)-6-hydroxycyclohex-2-en-1-ylidene]ethanenitrile 
• 561023-24-3 (2E)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile 
• 930117-56-9 (2E)-{(4R,5R,6S)-4,5-(cyclohexylidenedioxy)-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]-cyclohex-2-en-1-ylidene}ethanenitrile 
• 930117-57-0 (2E)-[(4R,5R,6S)-4,5-dihydroxy-6-{[2,3,4,6-tetrakis-O-(2-methylpropanoyl)-β-D-glucopyranosyl]oxy}-cyclohex-2-en-1-ylidene]ethanenitrile 

Downstream Products

• 61371-55-9 griffonilide 
• 50-99-7 D-glucose 
• 84799-67-7 hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ^1,α-acetonitrile 

Relevant academic research and scientific papers

Total synthesis of (2Z)-[(4R,5R,6S)-6-(β-D-glucopyranosyloxy)-4,5- dihydroxycyclohex-2-en-1-ylidene]ethanenitrile, a cyanoglucoside from Ilex warburgii

The total synthesis of the noncyanogenic cyanoglucoside 1, originally isolated from Ilex warburgii, was achieved in nine steps (9% overall yield), starting from an optically pure Diels-Alder adduct ((+)-3). The key step of the synthesis, the glycosidation

Total synthesis of (-)-lithospermoside

The total synthesis of the naturally occurring noncyanogenic cyanoglucoside (-)-lithospermoside (1) was achieved starting from optically pure oxatrinorbornenone (+)-2 in 12 steps and 10% overall yield. The key step of the synthesis, the glycosidation, turned out to be very sensitive to steric hindrance, and we had, therefore, to optimize the choice of the protection used for the two other OH functions of the aglycone. Finally, the desired β-D-glucoside 15 was obtained in a very good yield (72%) under Koenigs - Knorr-glycosidation conditions, closely related to those used for the total synthesis of (-)-bauhinin.