944471-84-5

Upstream product

• 5463-33-2 D-galactose-diethyl-dithioacetal 
• 100-39-0 benzyl bromide 
• 59-23-4 D-Galactose 
• 10257-28-0 D-Galactose 

Downstream Products

• 153093-36-8 2,3,4,5,6-penta-O-benzyl-aldehydo-D-galactose 
• 1421705-08-9 1,1'-dideoxy-2,3,4,5,6-penta-O-benzyl-D-galacto-hept-1'-ynitol 
• 1421705-09-0 1,1'-dideoxy-1'-(dibenzylphosphinyl)-2,3,4,5,6-penta-O-benzyl-D-galacto-hept-1'-ynitol 
• 1421705-12-5 (E)-1,1'-dideoxy-1'-(dibenzylphosphinyl)-2,3,4,5,6-penta-O-benzyl-D-galacto-hept-1'-enitol 
• 1421705-13-6 (Z)-1,1'-dideoxy-1'-bromo-2,3,4,5,6-penta-O-benzyl-D-galacto-hept-1'-enitol 
• 1421705-14-7 (E)-1,1'-dideoxy-1'-bromo-2,3,4,5,6-penta-O-benzyl-D-galacto-hept-1'-enitol 
• 1421705-18-1 (1R,1'R)-1'-(dibenzylphosphinyl)-2,3,4,5,6-penta-O-benzyl-D-galacto-heptitol 
• 1421705-19-2 (1R,1'S)-1,1'-oxiranyl-1'-(dibenzylphosphinyl)-2,3,4,5,6-penta-O-benzyl-D-galacto-heptitol 
• 1421705-32-9 (1’S)-dibenzyl C-(2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)hydroxymethanephosphonate 
• 1421705-33-0 (1’S)-dibenzyl C-(2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-1'-acetoxymethanephosphonate 
• 1421705-36-3 (E)-1,1'-dideoxy-1'-(dibenzylphosphinyl)-1’-(benzyloxycarbonyl)-2,3,4,5,6-penta-O-benzyl-D-galacto-hept-1'-enitol 
• 1421705-37-4 (Z)-1,1'-dideoxy-1'-(dibenzylphosphinyl)-1’-(benzyloxycarbonyl)-2,3,4,5,6-penta-O-benzyl-D-galacto-hept-1'-enitol 
• 944471-85-6 C₅₆H₆₀O₈PN 

Relevant academic research and scientific papers

Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.

Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction

An efficient and regioselective approach for the construction of synthetically important γ-lactone glycosides is reported from unprotected aldoses through a new debenzylative lactonization (DBL) reaction. The scope and limitations of this DBL reaction are described starting from a series of commercially available hexoses (l-fucose, d-galactose, d-glucose) and pentoses (d-arabinose, d-ribose, d-lyxose, d-xylose) to afford the corresponding γ-lactones in good yields and without concomitant δ-lactone formation.

Reversible and efficient inhibition of UDP-galactopyranose mutase by electrophilic, constrained and unsaturated UDP-galactitol analogues

A series of UDP-galactitols were designed as analogues of high-energy intermediates of the UDP-galactopyranose mutase (UGM) catalyzed furanose/pyranose interconversion, an essential step of Mycobacterium tuberculosis cell wall biosynthesis. The final compounds structurally share the UDP and the galactitol substructures that were connected by four distinct electrophilic connections (epoxide, lactone and Michael acceptors). All molecules were synthesized from a common perbenzylated acyclic galactose precursor that was derivatized by alkenylation, alkynylation and cyclopropanation. The inhibition study against UGM could clearly show that slight changes in the relative orientation of the UDP and the galactitol moieties resulted in dramatic variations of binding properties. Compared to known inhibitors, the epoxide derivative displayed a very tight, reversible, inhibition profile. Moreover, a time-dependent inactivation study showed that none of these electrophilic structures could react with UGM, or its FAD cofactor, the catalytic nucleophile of this still intriguing reaction. Shedding inhibitors: UDP-Galactopyranose mutase (UGM) is a validated target for treating tuberculosis. Its mechanism involves formation of a key covalent FAD-substrate intermediate, 1. A series of electrophilic UDP-galactitols were synthesized and assayed as inhibitors or inactivators of UGM. Strong inhibitions were observed, especially with epoxide 2. Interestingly, none of the molecules displayed an irreversible inhibition mode. Copyright

Synthesis of acyclic galactitol- and lyxitol-aminophosphonates as inhibitors of UDP-galactopyranose mutase

UDP-galactopyranose mutase (UGM) catalyzes the isomerization of UDP-galactopyranose (UDP-Galp) into UDP-galactofuranose (UDP-Galf), an essential step of the mycobacterial cell wall biosynthesis. Acyclic alditol-aminophosphonates in the d-galactose and d-l