145121-54-6

Upstream product

• 71020-96-7 6-O-benzyl-1,2:3,4-di-O-isopropylidene-β-D-psicofuranose 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 2179-92-2 tri-n-butyltin cyanide 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 364635-30-3 ((3aR,4S,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol 

Relevant academic research and scientific papers

The Regioselective Opening of 5-O-Benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose With Organostannanes

The trimethylsilyl triflate mediated regioselective opening of 5-O-benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose with organostannanes is presented.Hydrolysis of the initially formed 1-O-trimethylsilyl ether yields the products of S- and C-glycosidation with predominantly β-stereochemistry in good yields.The unusual addition of acetonitrile to the intermediate oxonium ion when the reaction is performed in this medium is also outlined.

Stereocontrolled Synthesis of Spirodihydrouracil Nucleoside

Synthesis of the spiro-dihydrouracil derivative of (+)-hydantocidin (2) is described.The pivotal step is a Lewis acid-mediated C-glycosidation of the protected D-psicose 3 with trimethylsilyl cyanide, which proceeded in good yield and β-selectivity.Synthe