279684-80-9

Upstream product

• 279684-66-1 (3S,4R,5S)-1-(trimethylsilyl)-4,5-epoxyhex-1-yn-3-ol 
• 332061-61-7 Benzoic acid (1R,2R,3S)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester 
• 279684-70-7 (2R,3R,4S)-3,4-bis(tert-butyldimethylsiloxy)-hex-5-yn-2-ol 
• 279684-95-6 Benzoic acid (1R,2S,3S)-2,3-dihydroxy-1-methyl-5-trimethylsilanyl-pent-4-ynyl ester 
• 279684-68-3 (2R,3R,4S)-hex-5-yn-2,3,4-triol 2-benzoate ester 
• 53723-96-9 (2E)-6-(trimethylsilyl)hex-2-en-5-yn-4-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 279684-76-3 3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-ribo-hex-1-enitol 
• 279684-79-6 (2R,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yne-2,3-diol 2-benzoate ester 

Downstream Products

• 389860-85-9 Benzoic acid (1R,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-((2S,4S,5R,6R)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-pent-4-ynyl ester 
• 71-63-6 digitoxin 

Relevant academic research and scientific papers

Convergent synthesis of digitoxin: Stereoselective synthesis and glycosylation of the digoxin trisaccharide glycal

Tungsten-catalyzed alkynol cycloisomerization and iterative acid-catalyzed stereoselective glycosylations form the basis of a revolutionary new strategy for oligosaccharide synthesis. The method has been successfully applied to a highly convergent synthesis of Digitalis 2-deoxyglycosides.

Stereoselective glycosylations of a family of 6-deoxy-1,2-glycals generated by catalytic alkynol cycloisomerization

Photolysis of 0.25 equiv of W(CO)6 in the presence of tertiary amines (triethylamine or DABCO) and highly functionalized terminal alkynyl alcohols catalyzes single-step, high-yield cycloisomerization to endocyclic enol ethers. This transformati