104976-70-7

Upstream product

• 104976-69-4 2,3,4-Tri-O-benzyl-5,6-O-isopropyliden-D-glucose-diethyldithioacetal 
• 100-39-0 benzyl bromide 
• 1049006-96-3 C₅₉H₆₆O₁₁ 
• 1049006-94-1 C₅₉H₆₆O₁₁ 
• 908836-17-9 (2S,3R,4R)-2,3,4-tris(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)butan-1-ol 
• 187103-77-1 2,3,4-tri-O-benzyl-D-glucitol 
• 4258-03-1 5,6-O-isopropylidene-D-glusose diethyl dithioacetal 

Downstream Products

• 104976-73-0 3,4,5-Tri-O-benzyl-1-desoxy-6,7-O-isopropyliden-D-gluco-2-heptosulose-1-phosphonsaeure-dimethylester 
• 1049006-95-2 methyl 2,3,4,9,10,11-hexa-O-benzyl-7,8-dideoxy-7,8-didehydro-12,13-O-isopropylidene-α-D-gluco-D-gluco-tridec-7(E)-eno-1,5-pyranosid-6-ulose 
• 104976-71-8 [(3S,4R,5R)-3,4,5-Tris-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-pentyl]-phosphonic acid dimethyl ester 

Relevant academic research and scientific papers

Optimized synthesis of a pentafluoro-gem-diol and conversion to a CF2Br-glucopyranose through trifluoroacetate-release and halogenation

Pentafluoro-gem-diols are substrates that enable the synthesis of valuable difluoromethylene-containing organic molecules through the release of trifluoroacetate. Currently, only one synthetic strategy is available to assemble these important precursors.

Synthesis of higher carbon sugars. Unexpected rearrangement of higher sugar allylic alcohols

Coupling of a sugar phosphonate with a sugar aldehyde afforded a C13-higher sugar enone. Reduction of the carbonyl function provided both stereoisomeric allylic alcohols. Inversion of the configuration at the carbinol centre in these derivatives did not yield the expected SN2 product, but proceeded with rearrangement to the tetrahydrofuran derivative.

Cyclitol Reactions, XIII.- Synthesis of Pseudosugars from D-Glucose by Intramolecular Horner-Emmons Olefination

The reaction of the aldehyde 3, prepared from D-glucose diethyl dithioacetal via 1 and 2, with lithium dimethyl methylphosphonat yields the adduct 4.Conversion of 4 into 9 followed by Swern oxidation results in the enone 6.Hydrogenation of 6 leads to pseu