499120-93-3

Upstream product

• 137344-85-5 5,6-dideoxy-3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-hexafuranose 
• 64638-65-9 5,6-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranos-3-ulose 
• 1826-67-1 vinyl magnesium bromide 
• 16749-42-1 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 

Downstream Products

• 660842-23-9 (3S,4S,5R)-5-Benzyl-3-((4E,6E)-3-hydroxy-2-methyl-nona-4,6-dienoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one 
• 660842-22-8 (5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 
• 660842-20-6 (5S,8R,9R)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 
• 660842-19-3 (S)-5-((Z)-(1S,2S)-1,2-Bis-methoxymethoxy-hex-3-enyl)-2-((R)-1-methoxymethoxy-2-oxo-3-phenyl-propyl)-4-methyl-3-oxo-2,3-dihydro-furan-2-carboxylic acid amide 
• 660842-18-2 (5S,8R,9S)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-9-methoxymethoxy-3-methyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione 
• 660842-24-0 (2S,3S,4R)-4-benzyl-2-hydroxy-2-[(4E,6E)-3-hydroxy-2-methylnona-4,6-dienoyl]-3-triethylsiloxy-4-butanolide 
• 660842-25-1 (5S,8R,9S)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-3-methyl-9-triethylsiloxy-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione 
• 660842-28-4 (5S,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 
• 660842-27-3 (5S,8R,9S)-8-benzyl-2-[(1E,3E)-hexa-1,3-dienyl]-9-methoxymethoxy-3-methyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione 
• 499121-02-7 (3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one 
• 499121-03-8 (3S,4S,5R)-5-Benzyl-3-hydroxy-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-4-triethylsilanyloxy-dihydro-furan-2-one 
• 499121-04-9 (5S,8R,9S)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-2-hydroxy-3-methyl-9-triethylsiloxy-1,7-dioxaspiro[4.4]nonane-4,6-dione 
• 499120-89-7 (5S,8R,9S)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-3-methyl-9-triethylsiloxy-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione 
• 499121-08-3 (2R,3S,4R)-4-benzyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-bis(triethylsiloxy)-4-butanolide 

Relevant academic research and scientific papers

Total syntheses of natural pseurotins A, F2, and azaspirene

We describe the total syntheses of natural pseurotins A and F2, inhibitors of chitin synthase, both of which possess an unusual 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione ring system. The total syntheses of these spiro-hetereocyclic natural produ

Stereocontrolled synthesis of a highly functionalized 1,7-dioxaspiro[4.4]Nonane derivative related to antibiotic pseurotins

For a total synthesis of pseurotins, unusual heterospirocyclic antibiotics, a key intermediate (5), having a highly functionalized 1,7-dioxaspiro-[4.4]nonane structure, has been synthesized from diacetone D-glucose.

Diacetone glucose architecture as a chirality template I. Crucial effects of the intramolecular oxygens upon the LiAlH4 reduction of the propargyl alcohol of 3-C-ethynyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose derivatives

The facile as well as regio- and stereoselective reactivity of 3-C-ethynyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose derivatives for LiAlH4 reduction into the corresponding ethenyl derivatives were investigated. The effect of oxygen atoms on the reduction is discussed by means of semi-empirical MO calculation.