190188-91-1

Upstream product

• 190188-89-7 Bromo-acetic acid (1R,2S,4S,5R)-2-(tert-butyl-diphenyl-silanyloxy)-3-[(Z)-methoxyimino]-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester 
• 90405-80-4 tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-7-yloxy)-diphenyl-silane 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 149793-78-2 1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-β-D-arabino-hexopyran-3-ulose 
• 14440-51-8 1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose 
• 109-92-2 ethyl vinyl ether 
• 190188-88-6 (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose 

Downstream Products

• 190188-88-6 (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose 
• 190188-89-7 Bromo-acetic acid (1R,2S,4S,5R)-2-(tert-butyl-diphenyl-silanyloxy)-3-[(Z)-methoxyimino]-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester 
• 190188-87-5 (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(2'-bromo-prop-2'-enyl)-β-D-arabino-hexopyranose 
• 190188-95-5 (Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose 

Relevant academic research and scientific papers

Radical cyclisation onto C-3 of 1,6-anhydro-β-D-mannopyranose derivatives. Application to the formation of the C8a centre of (-)-tetrodotoxin

Starting from 1,6-anhydro-β-D-mannopyranose, compounds 7a-d, which have a ketoxime ether at C3 and a carbon radical precursor tethered to the hydroxyl group at position 2, were efficiently prepared. While alkyl π-radicals derived from 7a and 7b failed to cyclize, the vinyl σ-radicals derived from 7c and 7d underwent the desired 1,5-exo cyclization, affording advanced precursors of (-)-tetrodotoxin, This type of transformation should be useful for the formation of sterically crowded nitrogen-bearing carbon centers in carbohydrate-derived substrates.