1422178-91-3

Upstream product

• 37776-17-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 1422178-88-8 (1S,5S,6S,7R,9R)-5,6,9-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)octadec-3-yn-1-ol 
• 1422178-89-9 tert-butyldimethyl(((1S,5S,6S,7R,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-yl)oxy)silane 
• 1422178-90-2 (1S,5S,6R,7R,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-ol 
• 1319725-92-2 C₄₃H₆₂O₄Si 

Downstream Products

• 1422178-96-8 C₆₁H₇₆O₁₀ 
• 1422178-92-4 C₆₁H₇₆O₁₀ 

Relevant academic research and scientific papers

Synthesis of C(27)-C(38) fragment of aflastatin A

Efforts at finding out a strategy for the synthesis of the densely hydroxylated C(27)-C(48) fragment of aflastatin A have been described. The initial studies dealing with alkyne-epoxide coupling using a linear polyol epoxide resulted in a debenzylative cycloetherification leading to a C-arabinoside derivative. This problem has been addressed by applying an epoxide pendant on a furanosyl unit. With the model alkyne, the epoxide-alkyne coupling proceeded smoothly. Subsequently, following a sequence of [Pd]-mediated alkynone cycloisomerization/stereoselective hydroboration-oxidation, the synthesis of the central C(27)-C(38) fragment has been executed. When employed, the original C(33)-C(48) alkyne, the coupling and the cycloisomerizations are facile. However, the resulting glycals are unstable, thus warranting a revision in our approach.