125284-35-7

Upstream product

• 125284-33-5 tert-butyldimethylsilyl 5-deoxy-5-C-(methoxycarbonyl)-2,3:7,8-di-O-isopropylidene-D-threo-L-talo-α-octofuranoside 
• 125284-33-5 tert-butyldimethylsilyl 5-deoxy-5-C-(methoxycarbonyl)-2,3:7,8-di-O-isopropylidene-D-erythro-D-talo-α-octofuranoside 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 125284-32-4 (S)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-((3aS,4S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid methyl ester 
• 125284-31-3 (1R,4R,5S,6S,7S)-4-exo-<(1'S,2'R)-1'-Hydroxy-2',3'-(isopropylidenedioxy)propyl>-6-exo,7-exo-(isopropylidenedioxy)-2,8-dioxabicyclo<3.2.1>octan-3-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 125284-32-4 (R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid methyl ester 
• 125284-34-6 tert-butyldimethylsilyl 5-deoxy-5-C-(hydroxymethyl)-2,3:7,8-di-O-isopropylidene-D-threo-L-talo-α-octofuranoside 
• 125284-31-3 (1S,4S,5R,6R,7R)-4-exo-<(1'R,2'R)-1'-Hydroxy-2',3'-(isopropylidenedioxy)propyl>-6-exo,7-exo-(isopropylidenedioxy)-2,8-dioxabicyclo<3.2.1>octan-3-one 
• 108-24-7 acetic anhydride 
• 125284-44-8 tert-butyldimethylsilyl 5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-threo-L-talo-α-octofuranoside 

Relevant academic research and scientific papers

Highly Stereoselective Total Syntheses of Octoses and Derivatives

Mukaiyama cross aldolizations of (R)-2,3-O-isopropylideneglyceraldehyde (10) with (1R,4S,5R,6R)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicycloheptan-2-one ((+)-8) and to its enantiomer ((-)-8) were highly diastereoselective and led to the corresponding u,u,l or SYNCAT ((+)-11) and u,u,u or ANCAT ((-)-21) aldols, respectively.The results were interpreted in terms of extended open transition state models with (ul,lk) and (ul,ul) topicities, respectively, which minimize steric repulsions.Aldols (+)-11 and (-)-21 were converted into (tert-butyl)dimethylsilyl 6-O-acetyl-2,3:7,8-di-O-isopropylidene-D-glycero-L-talo-α-octofuranosid-5-ulose ((-)-18) and its D-talo diastereomer ((+)-28), respectively.Reduction of (-)-18 with LiEt3BH in THF gave, after deprotection, the known D-threo-L-talo-octose ((-)-4).Reduction of (-)-18 with (i-Bu)2AlH/THF gave, after deprotection, the unknown D-threo-D-allo-octose ((+)-5) with high stereoselectivity.Similarly, the unknown D-erythro-D-talo-octose ((+)-6) and D-erythro-L-allo-octose ((-)-7) were derived from (+)-28 through reduction with LiB(s-Bu)3H and (i-Bu)2AlH, respectively.