Synthesis and enzyme inhibition study of unnatural saturated and unsaturated C-alkyl pyrrolidine iminosugars from d-mannose derived nitrone. Issue 2 (15th February 2016)

• Record Type: Journal Article
• Authors: Das, Pintu; Kundooru, Somireddy; Pandole, Ravikant; Sharma, Sandeep K.; Singh, Bhupendra N.; Shaw, Arun K.
• Is Part Of: Tetrahedron, asymmetry. Volume 27:Issue 2/3(2016)
• Page Start: 101
• Page End: 106
• Publication Date: 2016-02-15
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2015.12.003
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: The C -alkylated biologically important pyrrolidine iminosugars have been synthesized from commercially availabled -mannose. The key step of this strategy involves the diastereoselective Grignard addition tod -mannose derived nitrone7 . These unnatural iminosugars have also been tested against several glycosidases and some of them showed weak inhibition against some glucosidases. Abstract : (3a S, 4 R, 6 R, 6a R )-4-(( R )-2, 2-Dimethyl-1, 3-dioxolan-4-yl)-2, 2-dimethyl-6-vinyltetrahydro-4 H -[1, 3]dioxolo[4, 5- c ]pyrrole: C14 H23 NO4 [ α ]D 28 = +6.7 ( c 2.5, CHCl3 ) Source of chirality:d -Mannose Absolute configuration: (3a S, 4 R, 6 R, 6a R ) Abstract : (3a S, 4 R, 6 R, 6a R )-4-(( R )-2, 2-Dimethyl-1, 3-dioxolan-4-yl)-2, 2-dimethyl-6-vinyldihydro-3a H -[1, 3]dioxolo[4, 5- c ]pyrrol-5(4 H )-ol: C14 H23 NO5 [ α ]D 28 = +6.6 ( c 1.8, CHCl3 ) Source of chirality:d -Mannose Absolute configuration: (3a S, 4 R, 6 R, 6a R ) Abstract : (3a S, 4 R, 6 R, 6a R )- tert -Butyl 4-(( R )-2, 2-dimethyl-1, 3-dioxolan-4-yl)-2, 2-dimethyl-6-vinyldihydro-3a H -[1, 3]dioxolo[4, 5- c ]pyrrole-5(4 H )-carboxylate: C19 H31 NO6 [ α ]D 28 = +91.0 ( c 0.91, CHCl3 ) Source of chirality:d -Mannose Absolute configuration: (3a S, 4 R, 6 R, 6a R ) Abstract : (3a S, 4 S, 6 R, 6a R )- tert -Butyl 4-(hydroxymethyl)-2, 2-dimethyl-6-vinyldihydro-3a H -[1, 3]dioxolo[4, 5- c ]pyrrole-5(4 H )-carboxylate: C15 H25 NO5 [ α ]D 28 = +34.6 ( c 0.4, CHCl3 ) Source of chirality:d -Mannose Absolute configuration: (3a S, 4 S, 6 R, 6a R ) Abstract : (3a S, 4 R, 6 R, 6a R )-5-Butyl-4-(( R )-2, 2-dimethyl-1, 3-dioxolan-4-yl)-2, 2-dimethyl-6-vinyltetrahydro-3a H -[1, 3]dioxolo[4, 5- c ]pyrrole: C18 H31 NO4 [ α ]D 28 = +47.0 ( c 0.2, CHCl3 ) Source of chirality:d -Mannose Absolute configuration: (3a S, 4 R, 6 R, 6a R ) Abstract : (2 R, 3 S, 4 R, 5 R )-2-(( R )-1, 2-Dihydroxyethyl)-5-vinylpyrrolidine-3, 4-diol: C8 H15 NO4 [ α ]D 28 = +20.4 ( c 0.15, H2 O) Source of chirality:d -Mannose Absolute configuration: (2 R, 3 S, 4 R, 5 R ) Abstract : (2 S, 3 S, 4 R, 5 R )-2-(Hydroxymethyl)-5-vinylpyrrolidine-3, 4-diol: C7 H13 NO3 [ α ]D 28 = +65.4 ( c 0.3, H2 O) Source of chirality:d -Mannose Absolute configuration: (2 R, 3 S, 4 R, 5 R ) Abstract : (2 R, 3 S, 4 R, 5 R )-1-Butyl-2-(( R )-1, 2-dihydroxyethyl)-5-vinylpyrrolidine-3, 4-diol: C12 H23 NO4 [ α ]D 28 = +58.2 ( c 0.3, H2 O) Source of chirality:d -Mannose Absolute configuration: (2 R, 3 S, 4 R, 5 R ) Abstract : (2 R, 3 S, 4 R, 5 R )-2-(( R )-1, 2-Dihydroxyethyl)-5-ethylpyrrolidine-3, 4-diol: C8 H17 NO4 [ α ]D 28 = +105.2 ( c 0.3, H2 O) Source of chirality:d -Mannose Absolute configuration: (2 R, 3 S, 4 R, 5 R ) Abstract : (2 R, 3 R, 4 S, 5 S )-2-Ethyl-5-(hydroxymethyl)pyrrolidine-3, 4-diol: C7 H15 NO3 [ α ]D 28 = +3.9 ( c 0.3, H2 O) Source of chirality:d -Mannose Absolute configuration: (2 R, 3 R, 4 R, 5 R ) Abstract : (2 S, 3 S, 4 R, 5 R )-1-Butyl-2-(( R )-1, 2-dihydroxyethyl)-5-ethylpyrrolidine-3, 4-diol: C12 H25 NO4 [ α ]D 28 = +1.4 ( c 0.3, H2 O) Source of chirality:d -Mannose Absolute configuration: (2 S, 3 S, 4 R, 5 R )