A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP

Synthesis of Novel Iminosugar‐Based Trehalase Inhibitors by Cross‐Metathesis Reactions

“…[20] Final carbamoylation of intermediate 29 by Cbz-chloride in water/dioxane [21] afforded 24 (80 %). [20] On the contrary, the synthesis of β-C-allyl iminoribofuranosyl derivative 25 is not reported in the literature and is presented here from nitrone 30, [22] as illustrated in Scheme 4B. The Grignard reaction of nitrone 30 occurred with total stereoselectively and only the anti isomer was formed, according to the expected stereochemical outcome; reduction of hydroxylamine 31 to the corresponding amine 32 followed by carbamoylation afforded β-C-allyl iminoribofuranosyl derivative 25 suitable to be employed in the CM reaction.…”

Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-d-glucosaminidase inhibitors

“…Flash column chromatography was performed using Macherey-Nagel silica gel 60 (15e40 mm). NMR experiments were recorded with a Bruker AM-400 spectrometer at 400 MHz for 1 H nuclei and at 100 MHz for 13 NMR multiplicities are reported using the following abbreviations: b¼broad, s¼singulet, d¼doublet, t¼triplet, q¼quadruplet, m¼multiplet. HRMS were recorded on a Bruker microTOF spectrometer, using Tuning-Mix as reference.…”

“…4, 128.4, 127.8, 127.7, 127.6, 127.5, 127.4 (CH ar ) 81.5 (2C, (C(CH 3 ) 3 , Boc), 80.5 (2C, C 4 , C 4 0 ), 74.4 (2C, C 3 , C 3 0 ), 73.9, 72.9 (CH 2 Ph, 72.0 (2C, C 5 , C 5 0 ) 68.9 (2C, C 8 , C 8 0 ), 66.1 (2C, C 6 , C 6 0 ), 57.6 (2C, C 2 , C 2 0 ), 44.7 (2C, C 7 , C 7 0 ), 28.2 (CH 3 , Boc); ESI-HRMS calcd for C 33 1.9. (3R,4S,5R,6R,7R)-3-Azido-1-benzyl-5,6-bis(benzyloxy)-7-((benzyloxy)methyl)azepan-4-ol (13) To a solution of 6 (42 mg, 0.071 mmol) in CH 2 Cl 2 (4 mL) was added trifluoroacetic acid (2 mL) and the obtained solution was stirred at room temperature for 1 h. The solution was evaporated and co-evaporated with toluene (3Â5 mL). The residue was dissolved in EtOAc/H 2 O (4/0.4 mL) and K 2 CO 3 (49 mg, 0.355 mmol), BnBr (13 mL, 0.107 mmol) were added respectively.…”

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

“…[82] More recently, the hydrocyanation of polyhydroxylated five-membered cyclic nitrones has been used for preparing enantiopure 2-aminomethyl pyrrolidines of synthetic and biological interest [19a,66] such as nitrogenated analogues of glycosidase inhibitor DMDP [83] and stereoisomers of pochonicine inhibitors of β-Nacetylhexosaminidases. [84] The addition of trimethylsilylcyanide to cyclic ketonitrones provided an entry to pyrrolidines bearing quaternary centers (Scheme 19).…”