369630-44-4

Upstream product

• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 369630-59-1 methyl [3-O-benzyl-5-(tert-butyldiphenylsilyloxymethylene)-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanos]uronate 
• 369630-58-0 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 219584-24-4 1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethanone 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Relevant academic research and scientific papers

Synthesis of sugar-derived 2′- and 3′-substituted furans and their application in Diels - Alder reactions

A convenient synthesis of 2′- and 3′-furyl sugars in which the furan and the sugar parts are directly connected is presented. The key step comprises HF-py-induced cyclization of α,β-unsaturated carbonyl compounds (ketones or aldehydes) possessing terminal hydroxymethylene groups protected as TBDPS ethers. Treatment of such furan derivatives with N-phenylmaleimide under high-pressure conditions (11 kbar) produces the corresponding [4+2] adducts, with the endo forms predominating. At p = 1 atm and T = 20 °C, however, the exo isomers are formed as the main products. The [4+2] adducts undergo retro Diels-Alder reactions at elevated temperatures at atmospheric pressure.