Online citations, reference lists, and bibliographies.
← Back to Search

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

Sahadev S. Chirke, Sahadev S. Chirke, A. Rajender, J. K. Lakshmi, B. V. Rao, B. V. Rao
Published 2015 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy
Share
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.
This paper references
10.1021/JM0409019
Functionalized pyrrolidines inhibit alpha-mannosidase activity and growth of human glioblastoma and melanoma cells.
Hélène Fiaux (2005)
10.1021/OL0625482
Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays.
J. A. Castillo (2006)
10.1016/J.BMC.2003.10.003
Syntheses of tetrahydroxyazepanes from chiro-inositols and their evaluation as glycosidase inhibitors.
G. Painter (2004)
10.1055/S-1993-25927
Deoxyiminoalditols from Aldonolactones; II. Preparation of 1,4-Dideoxy-1,4-iminohexitols with D- and L-Galacto and D- and L-Ido Configuration: Potential Glycosidase Inhibitors
I. Lundt (1993)
10.1016/J.ANTIVIRAL.2006.03.016
Antiviral effects of glycosylation and glucose trimming inhibitors on human parainfluenza virus type 3.
Y. Tanaka (2006)
10.1016/J.TETLET.2003.11.053
Efficient stereodivergent synthesis of 1,4-dideoxy-1,4-iminohexitols from an (S)-glyceraldimine
R. Badorrey (2004)
10.1006/ABBI.2000.1930
Kinetic and functional characterization of 1,4-dideoxy-1, 4-imino-d-arabinitol: a potent inhibitor of glycogen phosphorylase with anti-hyperglyceamic effect in ob/ob mice.
K. Fosgerau (2000)
10.1021/JA00102A063
trans-2,3-cis-3,4-Dihydroxyproline, a New Naturally Occurring Amino Acid, Is the Sixth Residue in the Tandemly Repeated Consensus Decapeptides of an Adhesive Protein from Mytilus edulis
S. W. Taylor (1994)
10.1016/J.ANTIVIRAL.2006.01.013
Distinct thymidine kinases encoded by cowpox virus and herpes simplex virus contribute significantly to the differential antiviral activity of nucleoside analogs.
M. Prichard (2006)
10.1073/PNAS.77.5.2370
2,3-trans-3,4-trans-3,4-Dihydroxy-L-proline: An amino acid in toxic peptides of Amanita virosa mushrooms.
A. Buku (1980)
10.1016/S0957-4166(02)00033-2
Asymmetric synthesis of 1,4-dideoxy-1,4-imino-d-ribitol via stereoselective addition of allylphenylsulfone to an aryl N-sulfinylimine
R. Kumareswaran (2002)
10.1021/JM00013A012
N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
N. Asano (1995)
10.1016/J.TETASY.2012.04.009
Total synthesis of the acetyl derivatives of lyxo-(2R,3R,4R)-phytosphingosine and (−)-jaspine B
G. Rao (2012)
10.1016/S0040-4020(01)81716-6
Polyhydroxylated pyrrolidines from sugar lactomes: Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol from d-galactonolactone and syntheses of 1,4-dideoxy-1,4-imino-d-allitol, 1,4-dideoxy-1,4-imino-d-ribitol, and (2s,3r,4s)-3,4-dihydroxyproline from d-gulonolactone
G. Fleet (1988)
10.1021/BI00555A036
Virotoxins: actin-binding cyclic peptides of Amanita virosa mushrooms.
H. Faulstich (1980)
10.1016/j.bmc.2008.05.056
N-Arylmethyl substituted iminoribitol derivatives as inhibitors of a purine specific nucleoside hydrolase.
A. Goeminne (2008)
10.2174/1389200043335513
Glycosidase inhibitors as potential HIV entry inhibitors?
I. Robina (2004)
10.1002/3527601740
Iminosugars as Glycosidase Inhibitors
A. Stuetz (1998)
10.1016/J.TET.2013.11.004
A divergent approach for the synthesis of some polyhydroxy pyrrolidines and piperidines from ribosylamine
Sahadev S. Chirke (2014)
10.1021/JO025538X
Toward a general strategy for the synthesis of 3,4-dihydroxyprolines from pentose sugars.
C. Taylor (2002)
10.1016/0040-4039(91)80024-Z
A new enantioselective synthesis of (4S, 5S)-5-(N-Boc)-amino-6-cyclohexyl-4-hydroxy-hexanoic acid lactone, a hydroxyethylene dipeptide isostere precursor
H. Kotsuki (1991)
10.1097/MJT.0B013E318172886D
Iminosugars-From Synthesis to Therapeutic Applications
V. Ranade (2009)
10.2337/diab.31.3.249
The Effect of Chronic α-Glycosidase Inhibition on Diabetic Nephropathy in the db/db Mouse
S. Lee (1982)
10.1016/J.CHEMBIOL.2004.07.009
Discovery of picomolar slow tight-binding inhibitors of alpha-fucosidase.
Chuan-Fa Chang (2004)
10.1002/EJOC.201201342
A Divergent and Stereoselective Approach for the Syntheses of Some Polyhydroxylated Indolizidine and Pyrrolizidine Iminosugars
A. Rajender (2013)
10.1016/S0960-894X(01)00477-2
Derivatives of (2R, 3R, 4S)-2-aminomethylpyrrolidine-3,4-diol are selective α-mannosidase inhibitors
F. Popowycz (2001)
10.1016/J.TETASY.2006.12.023
Enantioselective synthesis of hydroxylated pyrrolidines via Sharpless epoxidation and olefin metathesis
C. Murruzzu (2007)
10.1016/J.TETLET.2010.12.039
N,N′-Dichlorobis(2,4,6-trichlorophenyl)urea (CC-2) as a new reagent for the synthesis of pyrimidone and pyrimidine derivatives via Biginelli reaction
G. B. Rao (2011)
10.1016/j.bmc.2013.07.048
α-Glucosidase-inhibitory iminosugars from the leaves of Suregada glomerulata.
R. Yan (2013)
10.1016/S0040-4039(03)01366-2
Stereoselective synthesis of 1,4-dideoxy-1,4-imino-d-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline
A. Madhan (2003)
10.1039/b914958a
Synthesis and biological activity of naturally occurring α-glucosidase inhibitors.
D. Wardrop (2010)
10.1002/EJOC.200901320
Recent Developments in the Synthesis of Pyrrolidine‐Containing Iminosugars
Bridget L. Stocker (2010)
10.1016/S0957-4166(00)00113-0
Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application
N. Asano (2000)
10.1002/CHEM.200304718
Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes.
T. M. Chapman (2003)
10.1016/J.TET.2007.06.044
Synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, l-allitol and d-talitol: a stereo selective approach for azasugars
B. Chandrasekhar (2007)
10.1016/J.TETLET.2010.04.011
A new stereoselective approach for N-benzyl amino(hydroxymethyl)cyclopentitols using RCM
J. P. Rao (2010)
10.1016/j.bmc.2010.03.009
Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as alpha-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies.
Claudia Bello (2010)
10.1016/j.bmc.2011.07.053
Anti-cancer activity of 5-O-alkyl 1,4-imino-1,4-dideoxyribitols.
Claudia Bello (2011)
10.1093/GLYCOB/CWI076
Imino sugar inhibitors for treating the lysosomal glycosphingolipidoses.
T. Butters (2005)
10.1016/J.TETASY.2011.07.009
A new stereoselective approach to aminocyclohexitols using RCM
A. Rajender (2011)
10.1016/S0031-9422(00)00451-9
Polyhydroxylated alkaloids -- natural occurrence and therapeutic applications.
A. Watson (2001)
10.1016/J.TETLET.2005.03.018
Stereoselective synthesis of (-)-gabosine C using a Nozaki-Hiyama-Kishi reaction and RCM
G. Ramana (2005)
10.1016/J.TETLET.2011.08.170
A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine
G. Rao (2011)
10.1042/0264-6021:3420545
Inhibition of glycogenolysis in primary rat hepatocytes by 1, 4-dideoxy-1,4-imino-D-arabinitol.
B. Andersen (1999)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar