- A divergent, short, and stereoselective approach to pyrrolidine iminosugars: Synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, d-ribitol, ethyl-erythritol, and (-)-2,3-trans-3-4-cis-dihydroxyproline
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A highly stereoselective addition of Grignard reagent on lactamine for the synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, d-ribitol, ethyl-erythritol, and (-)-2,3-trans-3-4-cis-dihydroxyproline has been described from commercially available d-ribose as a starting material.
- Chirke, Sahadev S.,Rajender, Anugula,Lakshmi, Jerripothula K.,Rao, Batchu Venkateswara
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- Stereospecific cyclization strategies for α,ε-dihydroxy-β-amino esters: Asymmetric syntheses of imino and amino sugars
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A range of biologically significant imino and amino sugars [1,4-dideoxy-1,4-imino-D-allitol, 3,6-dideoxy-3,6-imino-L-allonic acid, (3 R,4 S)-3,4-dihydroxy-L-proline, 1,5-anhydro-4-deoxy-4-amino-D-glucitol, and 1,5-anhydro-4-deoxy-4-amino-L-iditol] has bee
- Davies, Stephen G.,Foster, Emma M.,Lee, James A.,Roberts, Paul M.,Thomson, James E.
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- Enantioselective synthesis of hydroxylated pyrrolidines via Sharpless epoxidation and olefin metathesis
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The enantioselective synthesis of polyhydroxylated pyrrolidines from enantiomerically pure 2,3-epoxy-pent-4-en-1-ol 5 is described herein. The epoxy alcohol, readily available in any configuration by Sharpless epoxidation, was submitted to regioselective C-3 ring-opening with allyl amine, Boc-protection and ring-closing metathesis to yield dehydropyrrole derivative 7. From this key intermediate, 1,4-dideoxy-1,4-imino-d-ribitol (+)-3 and 1,4-dideoxy-1,4-imino-d-allitol (+)-4 were prepared in high yields. The enantiomers of these compounds can be obtained by the same sequence starting from an epoxy alcohol with the opposite configuration.
- Murruzzu, Caterina,Riera, Antoni
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p. 149 - 154
(2007/10/03)
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- Efficient stereodivergent synthesis of 1,4-dideoxy-1,4-iminohexitols from an (S)-glyceraldimine
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A stereodivergent synthesis of 1,4-dideoxy-1,4-imino-D-mannitol I and D-allitol III from an (S)-glyceraldimine, which is easily prepared from D-mannitol, has been achieved with overall yields of 62% and 49%, respectively. The synthesis is based on the add
- Badorrey, Ramón,Cativiela, Carlos,Díaz-De-Villegas, María D.,Díez, Roberto,Gálvez, José A.
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p. 719 - 722
(2007/10/03)
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- Stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline
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A stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol 1 and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline was achieved via the addition of vinylmagnesium bromide to the benzylimine derived from (R)-2,3-O-isopropylidene glyceraldehyde followed by N-allylation, ring-closing metathesis (RCM), and dihydroxylation.
- Madhan,Venkateswara Rao
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p. 5641 - 5643
(2007/10/03)
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- Method of inhibiting virus
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A group of five- and six-membered heterocyclic compounds having a nitrogen in the ring and 2 to 3 hydroxyl substituents on the ring are effective inhibitory agents of human immunodeficiency virus.
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- Potential Glycosidase Inhibitors: Synthesis of 1,4-Dideoxy-1,4-imino Derivatives of D-Glucitol, D- and L-Xylitol, D- and L-Allitol, D- and L-Talitol, and D-Gulitol
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Conversion of 2,3,5,6-tetra-O-benzyl-D-galactofuranose (19) into its oxime and subsequent treatment with methanesulphonyl chloride gave 2,3,5,6-tetra-O-benzyl-4-O-methylsulphonyl-D-galactonitrile (21).Reductive cyclization by sodium borohydride/cobalt(II)
- Buchanan, J. Grant,Lumbard, Keith W.,Sturgeon, Robert J.,Thompson, Deryk K.
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p. 699 - 706
(2007/10/02)
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