142010-65-9

Upstream product

• 142010-61-5 7-O-benzyl-6-deoxy-1,2:3,4-di-O-isopropylidene-7-C-(5-trimethylsilyl-2-furyl)-L-glycero-α-D-galacto-heptopyranose 
• 142010-62-6 7-O-benzyl-7-C-(but-3-en-4-olid-4-yl)-6-deoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-heptopyranose 
• 142010-60-4 (3aR,5R,5aS,8aS,8bR)-5-((R)-2-Benzyloxy-2-furan-2-yl-ethyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 100-39-0 benzyl bromide 
• 124582-54-3 6-deoxy-7-C-(2-furyl)-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-heptopyranose 
• 142010-63-7 7-O-benzyl-7-C-(but-2-en-4-olid-4-yl)-6-deoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-heptopyranose 
• 77-76-9 2,2-dimethoxy-propane 

Relevant academic research and scientific papers

The synthesis of 5-C-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-2,3-O-isopropylidene-D-allo-pentofuranose

Three approaches to the synthesis of deaminotunicamine and derivatives were developed.Tin tetrachloride condensation of 6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-heptodialdo-1,5-pyranose with 2-(trimethylsilyloxy)furan gave a mixture of stereoisomeric precursors.Condensation of 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose with the phosphate carbanion obtained from diethyl (2-furyl)methoxymethyl phosphonate led to 6-deoxy-7-C-(2-furyl)-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galactoheptopyranose (13).This was converted, via the "Δ2"-butenolide route, to a mixture of stereoisomeric 5-C-(6-deoxy-α-D-galactopyranos-6-yl)-pentono-1,4-lactones of the D-allo-and D-talo configuration.In the third approach, 13 was transformed by the "enulose" approach to deamino-tri-(o-isopropylidene)tunicamine.