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Intra-molecular Nitrone-olefin Cycloaddition Of D-glucose Derived Allylic Alcohol : Synthesis Of New Aminocyclohexitols

C. Chakraborty, V. P. Vyavahare, D. Dhavale
Published 2007 · Chemistry

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Abstract Diastereo- and regioselelective intra-molecular nitrone–olefin cycloaddition reaction of in situ generated N -benzylnitrones, obtained from d -glucose derived precursors 5a / 5b furnished dihydroxy functionalized isoxazolidines. The N – O bond reductive cleavage and removal of N / O -benzyl groups led to the formation of stereochemically well defined aminocyclohexitols.
This paper references
10.1016/S0040-4039(01)96961-8
A simple model for substituent effects in cycloaddition reactions. I. 1,3-dipolar cycloadditions
R. Sustmann (1971)
10.1039/A905706D
Stereocontrolled synthesis of polyhydroxylated hexahydro-1H-cyclopent[c]isoxazoles by intramolecular oxime olefin cycloadditions: an approach to aminocyclopentitols
P. J. Dransfield (1999)
10.1246/CL.1980.1407
NOVEL E–Z EQUILIBRIUM OF N-ALKYL-α-ALKOXYCARBONYLNITRONE IN SOLUTION
InouyeYoshinobu (1980)
10.1016/J.TETLET.2006.10.070
Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3,5-bishydroxymethyl cyclopentanol from d-glucose
B. Roy (2006)
10.1016/J.BMC.2003.12.016
Convenient synthesis and evaluation of glycosidase inhibitory activity of α- and β-galactose-type valienamines, and some N-alkyl derivatives
S. Ogawa (2004)
10.1021/JO0601617
Intramolecular 5-endo-trig aminomercuration of beta-hydroxy-gamma-alkenylamines: efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues.
Narayan S. Karanjule (2006)
10.1080/00304948509355467
RECENT SYNTHETIC APPLICATIONS OF NITRONES. A REVIEW
N. Balasubramanian (1985)
10.1021/JA0205378
Synthesis, structure, and biological evaluation of novel N- and O-linked diinositols.
B. Paul (2002)
10.1039/B205561A
The C7N aminocyclitol family of natural products.
T. Mahmud (2003)
10.7164/ANTIBIOTICS.29.319
Biosynthesis of aminocyclitol antibiotics.
K. Rinehart (1976)
10.1016/S0008-6215(00)90393-8
Synthesis of dl-penta-N,O-acetylvaliolamine and related branched-chain aminocyclitols
S. Ogawa (1986)
10.1021/OL034127F
Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes: incorporation of polyhydroxylated carbocyclic beta-amino acids into peptides.
R. Soengas (2003)
10.1016/S0040-4039(98)02539-8
Ring closing metathesis as an efficient approach to branched cyclitols and aminocyclitols: a short synthesis of valiolamine
O. Sellier (1999)
10.1021/JO050589Q
Pyridinium salt photochemistry in a concise route for synthesis of the trehazolin aminocyclitol, trehazolamine.
X. Feng (2005)
10.1021/OL991252B
Synthesis and Evaluation of Aminocyclopentitol Inhibitors of β-Glucosidases
O. Boss (2000)
10.1021/JA005746B
A new structural motif for the design of potent glucosidase inhibitors.
K. S. Tanaka (2001)
Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis: Novel Strategies in Synthesis
K. Torssell (1988)
10.1016/J.CARRES.2006.06.022
Synthesis of new analogues of salacinol containing a pendant hydroxymethyl group as potential glycosidase inhibitors.
Ravindranath Nasi (2006)
10.1021/CR970324E
Asymmetric 1,3-Dipolar Cycloaddition Reactions.
K. Gothelf (1998)
Nitrones, nitronates, and nitroxides
E. Breuer (1989)
10.1039/A827155Z
Carbocycles from carbohydrates via free radical cyclizations: new synthetic approaches to glycomimetics
A. Martínez-Grau (1998)
10.1016/S0040-4039(00)92386-4
Enantiospecific total synthesis of (-)-allosamizoline, and aminocyclitol moiety of the insect chitinase inhibitor allosamidin
M. Nakata (1991)
10.1021/JO981955R
CHIRAL CARBOCYCLIC NUCLEOSIDES FROM D-GLUCOSE: ENANTIODIVERGENT SYNTHESIS AND ONE-POT ENTRY OF DIMETHYLAMINO FUNCTIONALITY IN THE PURINE RINGS
A. Roy (1999)
10.1016/S0040-4039(01)00877-2
[1,3]-Dipolar intramolecular nitrone olefin cycloaddition reaction of a sugar-derived α,β-unsaturated ester: a new diastereo- and regioselective synthesis of an aminocyclopentitol
S. Jachak (2001)
10.1021/JO9711899
Acyclic Stereodifferentiation: Selective Construction of Tetrahydropyran/Oxepane via Intramolecular Nitrone-Alkene Cycloaddition of Acyclic 3-O-Allylmonosaccharides.
T. K. Shing (1998)
10.1016/J.TETLET.2004.07.087
Stereocontrolled synthesis of the aminocyclitol moiety of (+)-trehazolin via C–H insertion reaction of alkylidenecarbene
Megumi Akiyama (2004)
10.1016/J.TET.2006.06.078
PdCl2/CuCl2-catalysed chlorocyclisation of sugar-derived aminoalkenitols in the synthesis of new iminohexitols
P. Szolcsányi (2006)
10.1021/CR000446Y
Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides.
M. Ferrero (2000)
10.1021/JA00803A018
Origin of reactivity, regioselectivity, and periselectivity in 1,3-dipolar cycloadditions
K. Houk (1973)
10.1021/CR00016A004
AIDS-driven nucleoside chemistry.
D. M. Huryn (1992)
10.1021/JO0496547
RCM approaches toward the diastereoselective synthesis of vicinal trans-diaminocyclitols from L-serine.
X. Cong (2004)
10.1016/S0040-4039(01)01946-3
Synthesis of l-α-phosphatidyl-d-myo-inositol 3,5-bisphosphate from d-glucose
A. Nishikawa (2001)
10.1002/HLCA.19770600214
Synthese und Umwandlungen von Isoxazolidin‐Nucleosiden
A. Vasella (1977)
10.1016/J.TET.2003.09.049
Synthesis and glycosidase inhibitory activity of aminocyclitols with a C6- or a C7-ring
C. Gravier-Pelletier (2003)
10.1021/BK-1992-0494
Cycloaddition reactions in carbohydrate chemistry
R. Giuliano (1992)
10.1016/S0040-4039(99)02080-8
New accesses to l-iduronyl synthons
A. Lubineau (2000)
10.1039/B603545K
Synthesis of tetrahydroxy perhydroaza-azulenes: tandem Johnson-Claisen rearrangement of D-glucose-derived allylic alcohols.
Shankar D. Markad (2006)
10.1021/OL061022E
Stereodivergent syntheses of conduramines and aminocyclitols.
C. Alegret (2006)
10.1016/J.TETASY.2006.09.010
Straightforward chemo-enzymatic synthesis of new aminocyclitols, analogues of valiolamine and their evaluation as glycosidase inhibitors
Lahssen El Blidi (2006)
10.1016/S0040-4039(01)85753-1
Comprehensive organic chemistry : the synthesis and reactions of organic compounds
D. Barton (1978)
10.1021/JO048176X
1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues.
Narayan S. Karanjule (2005)
1,3-Dipolar Cycloaddition Chemistry
A. Padwa (1984)
10.1016/S0040-4020(01)88278-8
Diastereoselectivity in the intramolecular nitrone, oxime, and nitrile oxide cycloaddition reactions. Synthesis of amino inositol derivatives as α-glucosidase inhibitors
N. Peet (1991)
10.1021/JO01052A076
The Reaction of Free Carbonyl Sugar Derivatives with Organometallic Reagents. I. 6-Deoxy-L-idose and Derivatives1,2
M. Wolfrom (1962)
10.1002/HLCA.200490218
Cyclopentanes from N‐Aminoglyconolactams: Reaction Mechanism and Improved Access to Diazocyclopentanones
G. Hu (2004)
10.1002/1521-3765(20010903)7:17<3768::AID-CHEM3768>3.0.CO;2-C
AAA in KAT/DYKAT processes: first- and second-generation asymmetric syntheses of (+)- and (-)-cyclophellitol.
B. Trost (2001)
10.1002/1521-3765(20010417)7:8<1619::AID-CHEM16190>3.0.CO;2-4
Asymmetric induction of conduritols via AAA reactions: synthesis of the aminocyclohexitol of hygromycin A.
B. Trost (2001)
10.1201/9781482273588
Preparative carbohydrate chemistry
S. Hanessian (1997)
10.1002/1439-7633(20010504)2:5<365::AID-CBIC365>3.0.CO;2-M
Amino(hydroxymethyl)cyclopentanetriols, an Emerging Class of Potent Glycosidase Inhibitors—Part I: Synthesis and Evaluation of β‐D‐Pyranoside Analogues in the manno, gluco, galacto, and GlcNAc Series
M. Kleban (2001)
10.1039/A700389G
ENANTIOSPECIFIC SYNTHESIS OF (-)-5-EPI-SHIKIMIC ACID AND (-)-SHIKIMIC ACID
Shende Jiang (1997)
10.1016/S0040-4020(00)00981-9
Stereocontrolled 1,3-addition reaction of silyl ketene acetal to sugar nitrone: synthesis of d-gluco-homo-1-deoxynojirimycin and l-ido-homo-1-deoxynojirimycin
N. N. Saha (2001)
10.1351/pac197440040569
Orbital energy control of cycloaddition reactivity
R. Sustmann (1974)
10.1016/S0040-4039(01)02125-6
A norbornyl route to aminocyclohexitols: syntheses of diverse aminocarbasugars and ‘confused’ aminocarbasugars
G. Mehta (2002)
10.1021/JO060823S
Synthesis of pentahydroxy indolizidine alkaloids using ring closing metathesis: attempts to find the correct structure of uniflorine A.
Narayan S. Karanjule (2006)
10.1016/S0065-2318(08)60264-4
Structures and syntheses of aminoglycoside antibiotics.
S. Umezawa (1974)
10.1016/S0040-4039(00)91860-4
Access to polyhydroxylated cycloheptane derivatives through stereoselective nitrile oxide intramolecular cycloaddition. Synthesis of an analogue of calystegine B2
O. Duclos (1992)



This paper is referenced by
10.1021/JO502672X
Exploitation of in situ generated sugar-based olefin keto-nitrones: synthesis of carbocycles, heterocycles, and nucleoside derivatives.
Soumendra Nath Das (2015)
10.1080/00397910802281429
Synthesis of a New Family of Aminocyclitols from D-(-)-Quinic Acid
T. Shih (2008)
10.3762/bjoc.6.15
Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration
L. Kelebekli (2010)
10.1021/acs.chemrev.6b00543
Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry.
M. Berthet (2016)
10.1016/J.TETLET.2018.04.066
Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates
V. A. Dmitriev (2018)
10.1002/chem.201100418
A temperature-guided diastereoselectivity switch during the desymmetrization of meso-7-azabicyclo[2.2.1]heptadiene: new strategy towards the synthesis of aminocyclitols.
G. Pandey (2011)
10.1002/CHIN.200812209
Intramolecular Nitrone—Olefin Cycloaddition of D‐Glucose‐Derived Allylic Alcohol: Synthesis of New Aminocyclohexitols.
C. Chakraborty (2008)
10.1016/S0959-6380(08)80013-X
Chapter 5.7 Five-membered ring systems with O & N atoms
S. Cicchi (2008)
10.1002/EJOC.200800238
Recent Advances in the Chemistry of Aminocyclitols
Antonio Delgado (2008)
10.1016/J.TETLET.2011.03.141
Medium-ring aminocyclitols: a concise synthesis of nine-membered aminocarbasugar analogs and the solid-state supramolecular architectures of two key precursors
G. Mehta (2011)
10.1016/J.TET.2008.07.049
Synthesis of five and six membered aminocyclitols: stereoselective Michael and Henry reaction approach with d-glucose derived α,β-unsaturated ester
C. Chakraborty (2008)
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