144152-51-2

Upstream product

• 131940-20-0 (-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose 
• 98-88-4 benzoyl chloride 
• 14168-65-1 mannosan 
• 14440-51-8 1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose 
• 7225-53-8 (-)-1,6-anhydro-4-O-benzoyl-β-D-mannopyranose 
• 149793-72-6 1,6-anhydro-4-O-benzoyl-2-O-(p-methoxybenzyl)-β-D-mannopyranose 

Downstream Products

• 149883-63-6 (1R,2S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-eth-(E)-ylidene]-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]octan-2-ol 
• 149883-62-5 (1R,2S,4S,5R)-3-[2-Hydroxy-eth-(E)-ylidene]-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]octan-2-ol 
• 144152-57-8 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline 
• 144152-56-7 2'-methyl-(1,6-anhydro-3-deoxy-3-C-formyl-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline 
• 144152-54-5 (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-4-ene 
• 144152-55-6 2'-methyl-(1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-3-C-vinyl-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline 

Relevant academic research and scientific papers

Carbohydrates to carbocycles: Synthesis of the densely functionalized carbocyclic core of tetrodotoxin by radical cyclization of an anhydro sugar precursor

The core of tetrodotoxin is a densely functionalized carbocycle for which an annulated pyranose can be envisaged as a retron. The carbocyclic ring is constructed upon a rigid 1,6-anhydro template which permits the early introduction of the key angular nit

NOVEL REACTIONS OF CARBOHYDRATES DISCOVERED EN ROUTE TO NATURAL PRODUCTS

An approach to the synthesis of tetrodotoxin is described in which two key reactions are used to establish the densely functionalized carbocyclic ring.The -bicyclic framework of 1,6-anhydro mannopyranose serves as the the template, and in the first