Synthesis of N-sugar-substituted phthalimides and their derivatives from sugar azides and phthalic anhydride

Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit

“…As we terminated the first-generation approach, it was clear that the Gal-β-(1 → 3)-GalNAc bond was more difficult to install than we anticipated. In fact, with few exceptions, a large number of routine glycosylation procedures favor orthoester formation over glycosidic bond formation. − ,,,− One obscure tactic used to generate this bond is to mask the C2 amine of the galactosamine acceptor as an azide. , We incorporated this maneuver into a second-generation approach targeting 3 (Figure ). The plan called for Gal-β-(1 → 3)-GalNAc glycosidic bond formation early in the synthesis (step i ).…”

“…27−29,31,32,44−49 One obscure tactic used to generate this bond is to mask the C2 amine of the galactosamine acceptor as an azide. 27,50 We incorporated this maneuver into a second-generation approach targeting 3 (Figure 3). The plan called for Gal-β-(1 → 3)-GalNAc glycosidic bond formation early in the synthesis (step i).…”

Phthalic anhydride (PA): a valuable substrate in organic transformations

“…N -Sugar-substituted phthalimides ( 139 ) constructed in 2004 by Li's group via the reaction of PA ( 1 ) sugar azide ( 138 ) in a 15 : 1 molar ratio in the presence of tetrabutyl ammonium iodide (0.1 mmol, as catalyst) under essentially neutral conditions [which was performed by NaI (3 mmol) and Me 3 SiCl (1.5 mmol)] in dry acetonitrile at ambient temperature or 60 °C within 1–3 h with 78–92% yield (Scheme 49). 160…”

“…159 N-Sugar-substituted phthalimides (139) constructed in 2004 by Li's group via the reaction of PA (1) sugar azide (138) in a 15 : 1 molar ratio in the presence of tetrabutyl ammonium iodide (0.1 mmol, as catalyst) under essentially neutral conditions [which was performed by NaI (3 mmol) and Me 3 SiCl (1.5 mmol)] in dry acetonitrile at ambient temperature or 60 °C within 1-3 h with 78-92% yield (Scheme 49). 160 Kamal in 1994 also reported N-substituted phthalimides (139) from the reaction of the corresponding azides (138) and PA (1) in a 1 : 1 molar ratio, employing chlorotrimethylsilane and sodium iodide (in situ generation of iodotrimethylsilane) in acetonitrile at ambient temperature within 15 min with 95% yield. 161 Nguyen and coworkers in 2012 performed the bisaddition of pyridinyl lithium (140) to PA, which yielded the monoaddition product 3-hydroxyisobenzofuranone (143) and 3,3-bis(6-methylpyridin-2-yl)isobenzofuran-1(3H)-one (144) as the byproduct.…”

In vitro anticancer property of a novel thalidomide analogue through inhibition of NF-κB activation in HL-60 cells

“…Drugs and reagents A novel sugar-substituted thalidomide analogue, 1-O-methyl-2,3,4-tri-acetyl-6-tetrafluorophthalimido-6-deoxy-α-D-glucopyranose, named STA-35, was synthesized by condensation of tetrafluorophthalic anhydride with related 6-aminoglucose according to the literature [24] . Its structure was determined by 1 H, 13 C NMR, and mass spectrum and elementary analyses (C 21 H 19 O 10 NF 4 , 521.38, Figure 1).…”