473535-41-0

Upstream product

• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 473535-34-1 (2R,5S)-2-(1-oxoethyl)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran 
• 201536-71-2 1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose 
• 201472-26-6 (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 563-47-3 3-Chloro-2-methylpropene 
• 149198-05-0 (2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile 

Downstream Products

• 473535-42-1 (2R,5S)-2-[(R)-2-(2-oxopropyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran 
• 473535-45-4 (6R)-6-methyl-6-[(2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyloxy]methyl)tetrahydrofuran-2-yl]pyran-2[3H]-one 
• 473535-46-5 6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one 

Relevant academic research and scientific papers

Synthetic approach to analogues of the original structure of sclerophytin A

A route to analogues of the original structure of sclerophytin A is described. The β-anomer of dideoxyribosyl nitriles 10a,b (prepared from glutamic acid) was converted into the methyl ketone 11. Addition of a silylated acetylide to 11 in diethyl ether/trimethylamine gave mainly 22a. Alkylation with methallyl halide and ozonolysis gave the ketone 24, which was then converted by hydrogenation and a second ozonolysis into the keto aldehyde 26. A two-step aldol process afforded the desired 3-pyrone 27 in good overall yield. However, several methods for the conversion of this enone 27 into the desired sclerophytin analogue 2 failed.