701211-76-9

Upstream product

• 138769-92-3 cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene 
• 154784-39-1 (3aS,7aS)-4-iodo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 485400-33-7 (3R,4R,5S,6S)-1-iodo-3-O-benzyl-5-O,6-O-(propane-2,2-diyl)-cyclohex-1-ene-3,4,5,6-tetraol 
• 910564-72-6 (1S,2S,3S,6R)-6-Benzyloxy-4-iodo-cyclohex-4-ene-1,2,3-triol 
• 596834-80-9 (2'S,3'S,3R,4R,5S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohex-1-ene-3,4,5,6-tetraol 
• 165611-18-7 (3aS,4R,5R,7aS)-7-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol 
• 701211-75-8 (2'S,3'S,3R,4R,5R,6S)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-cyclohex-1-ene-3,4,5,6-tetraol 
• 431-03-8 dimethylglyoxal 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 701211-79-2 (2'S,3'S,3R,4R,5S)-1-methoxycarbonyl-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6,6-difluoro-cyclohex-1-ene-3,4,5-triol 
• 701211-78-1 (2'S,3'S,3R,4R,5S)-1-iodo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6,6-difluoro-cyclohex-1-ene-3,4,5-triol 

Relevant academic research and scientific papers

Arene cis-dihydrodiols-useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid

The synthesis of 6,6-difluoroshikimic acid (11) has been achieved in ten steps from the enantiopure diol 16, which is derived from enzymatic cis-dihydroxylation of iodobenzene. The versatility of the synthetic strategy has been demonstrated by the preparation of the known antimicrobial agent, (6S)-6-fluoroshikimic acid (5).

The synthesis of 6,6-difluoroshikimic acid

The synthesis of 6,6-difluoroshikimic acid (4) has been achieved in nine steps from the enantiopure diol 9, which is derived from microbial dihydroxylation of iodobenzene. The synthetic strategy has also been demonstrated to be applicable to the preparati