185671-86-7

Upstream product

• 154714-19-9 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 

Downstream Products

• 185671-89-0 2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid 
• 185671-88-9 5-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one 
• 185671-87-8 5-[(R)-16-((2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-heptadecyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one 

Relevant academic research and scientific papers

Synthesis of 2-hydroxy-6-{[(16R)-β-D-mannopyranosyloxy]heptadecyl}benzoic acid, a fungal metabolite with GABA(A) ion channel receptor inhibiting properties

An expeditious total synthesis of the physiologically active fungal metabolite 1 is described, The stereoselective formation of its β-D-mannopyranosidic linkage is achieved in two steps upon reaction of the hexopyranos-2-ulosyl bromide 15 with the glycosyl acceptor 13, followed by reduction of the resulting β-D-glycos-2-uloside 16. Alcohol 13 was efficiently prepared via a Suzuki reaction of the aryltriflate 11 with the 9-alkyl-9-BBN derivative 10.