Abstract
Michael-type addition of enamino esters to 3,4,6-tri-O -benzyl-2-nitro-d -glucal
under solvent-free conditions formed C -glycosides
in excellent yields with high stereoselectivity. Reduction of the
nitro group afforded the corresponding bicyclic 2-amino C -glycosides.
Key words
solvent-free -
C -glycosides - Michael-type addition
References and Notes
1a Kim J.-H.
Huang F.
Ly M.
Linhardt RJ.
J. Org. Chem.
2008,
73:
9497
1b Yuan X.
Linhardt RJ.
Curr. Top. Med.
Chem.
2005,
5:
1393
1c Hultin PG.
Curr. Top. Med. Chem.
2005,
5:
1299
1d Costantino V.
Fattorusso E.
Imperatore C.
Mangoni A.
J. Org. Chem.
2004,
69:
1174
1e Yang J.
Franck RW.
Bittman R.
Samadder P.
Arthur G.
Org.
Lett.
2001,
3:
197
1f Shuto S.
Yahiro Y.
Ichikawa S.
Matsuda A.
J. Org. Chem.
2000,
65:
5547
C -glycoside
synthesis, see:
2a Levy DE.
Fügedi P.
Strategies Towards C -Glycosides , In The Organic Chemistry of Sugars
Levy DE.
Fügedi P.
CRC Press;
Boca Raton:
2006.
p.269-348
2b Meo P.
Osborn
HMI.
Best Synthetic Methods: Carbohydrates
Elsevier Science
Ltd.;
New York:
2003.
p.337-384
2c Somsák L.
Chem. Rev.
2001,
101:
81
2d Du Y.
Linhardt RJ.
Tetrahedron
1998,
54:
9913 ; and references cited therein
2e Postema MHD.
C-Glycoside
Synthesis
CRC Press;
Boca Raton:
1995.
p.193-226
C -glycoside synthesis, see:
3a Dondoni A.
Massi A.
Acc. Chem. Res.
2006,
39:
451
3b Chambers DJ.
Evans GR.
Fairbanks AJ.
Tetrahedron: Asymmetry
2005,
16:
45
3c Schmidt RR.
Vankar YD.
Acc.
Chem. Res.
2008,
41:
1059
3d Lubin-Germain N.
Baltaze J.-P.
Coste A.
Hallonet A.
Lauréano H.
Legrave G.
Uziel J.
Augé J.
Org. Lett.
2008,
10:
725
3e Lin L.
He X.-P.
Xu R.
Chen G.-R.
Xie J.
Carbohydr.
Res.
2008,
343:
773
3f Gong H.
Gagné MR.
J. Am. Chem.
Soc.
2008,
130:
12177
3g Adriano S.
Vieira AS.
Fiorante PF.
Hough
TLS.
Ferreira FP.
Lüdtke DS.
Stefani HA.
Org. Lett.
2008,
10:
5215
3h Ichikawa S.
Hayashi R.
Hirano S.
Matsuda A.
Org. Lett.
2008,
10:
5107
3i Crich D.
Sharma I.
Org. Lett.
2008,
10:
4731
3j Mukherjee D.
Taneja SC.
Tetrahedron Lett.
2007,
48:
663
3k Yadav
JS.
Satyanarayana M.
Balanarsaiah E.
Raghavendra S.
Tetrahedron
Lett.
2006,
47:
6095
3l Yadav JS.
Reddy BVS.
Chary DN.
Madavi C.
Kunwar AC.
Tetrahedron Lett.
2009,
50:
81
4a Michael K.
Wittmann V.
Konig W.
Sandow J.
Kessler H.
Int. J. Pept. Protein Res.
1996,
48:
59
4b Allevi P.
Anastasia M.
Ciuffreda P.
Fiecchi A.
Scala A.
J.
Chem. Soc., Chem. Commun.
1988,
57
4c Yadav JS.
Redd BVS.
Srinivas M.
Divyavani C.
Kunwarb AC.
Madavi C.
Tetrahedron
Lett.
2007,
47:
8301
4d Yadav JS.
Redd BVS.
Satheesh G.
Narasimhulu G.
Portier Y.
Madhavi C.
Kunwar AC.
Tetrahedron Lett.
2008,
49:
3341
5a Elassar A.-ZA.
El-Khair AA.
Tetrahedron
2003,
59:
8463
5b Makabe O.
Murai Y.
Fukatus S.
Heterocycles
1979,
13:
239
5c Jensen EM.
Papadopoulos EP.
Heterocycles
1983,
20:
2233
5d Akiyama Y.
Abe J.
Takanu T.
Kawasaki T.
Sakamoto M.
Chem. Pharm.
Bull.
1984,
32:
2821
6a Jensen T.
Madsen R.
J. Org. Chem.
2009,
74:
3990
6b Kamata K.
Nakagawa Y.
Yamaguchi K.
Mizuno N.
J. Am. Chem. Soc.
2008,
130:
15304
6c Kuhn KM.
Grubbs RH.
Org.
Lett.
2008,
10:
2075
6d Mukherjee D.
Shah BA.
Gupta P.
Taneja SC.
J. Org. Chem.
2007,
72:
8965
6e Tanaka K.
Toda F.
Chem. Rev.
2000,
100:
1025
6f Loupy A.
Top.
Curr. Chem.
1999,
206:
153
6g Singh NB.
Singh RJ.
Singh NP.
Tetrahedron
1994,
50:
6441
6h Ramamurthy V.
Venkatesan K.
Chem. Rev.
1987,
87:
433
7a Massi A.
Nuzzi A.
Dondoni A.
J.
Org. Chem.
2007,
72:
10279
7b Aich U.
Loganathan D.
Carbohydr. Res.
2006,
341:
19
7c Lin H.-C.
Chang C.-C.
Chen J.-Y.
Lin C.-H.
Tetrahedron: Asymmetry
2005,
16:
297
7d de Oliveira RN.
de Freitas Filho JR.
Srivastava RM.
Tetrahedron
Lett.
2002,
43:
2141
7e Sowmya S.
Balasubramanian KK.
Synth. Commun.
1994,
24:
2097
N -, O -, S -, P - and C -glycosides. For representative examples,
see:
8a Winterfeld GA.
Das J.
Schmidt RR.
Eur. J. Org. Chem.
2000,
3047
8b Khodair AI.
Pachamuthu K.
Schmidt RR.
Synthesis
2004,
53
8c Winterfeld GA.
Khodair AI.
Schmidt RR.
Eur. J. Org. Chem.
2003,
1009
8d Barroca N.
Schmidt RR.
Org. Lett.
2004,
6:
1551
8e Pachamuthu K.
Figueroa-Perez I.
Ali IAI.
Schmidt RR.
Eur.
J. Org. Chem.
2004,
3959
8f Pachamuthu K.
Schmidt RR.
Synlett
2003,
1355
9 Winterfeld GA.
Schmidt RR.
Angew. Chem. Int.
Ed.
2001,
40:
2654
10a Cai C.
Soloshonok VA.
Hruby VJ.
J. Org. Chem.
2001,
66:
1339
10b Sundararajan G.
Prabagaran N.
Org. Lett.
2001,
3:
389
10c Hoz S.
Acc.
Chem. Res.
1993,
26:
69
11 General experimental procedure: A
mixture of 2-nitro-d -glucal 1 (1.0
mmol) and enamino ester 2 (1.2 mmol) was heated
to the specified temperature in a silicone oil bath, as indicated
in Table 1. The progress of the reaction was monitored by TLC. Upon
completion, the reaction mixture was cooled to room temperature
and purified by column chromatography using a mixture of ethyl acetate
and petroleum ether as the eluent to furnish the target product.
12 Li A.-H.
Moro S.
Melman N.
Ji XD.
Jacobson KA.
J. Med. Chem.
1998,
41:
3186
13 The crystal structures of 3d and 3i have
been deposited at the Cambridge Crystallographic Data Centre and
allocated the deposition numbers CCDC 778452 and 778453, respectively.
14a Jones K.
Newton RF.
Yarnold CJ.
Tetrahedron
1996,
52:
4133
14b Célérier J.-P.
Deloisy E.
Lhommet G.
Maitte P.
J. Org. Chem.
1979,
44:
3089
15
Hutchinson IS.
Matlin SA.
Mete A.
Tetrahedron Lett.
2001,
42:
1773
16a Pachamuthu K.
Gupta A.
Das J.
Schmidt RR.
Vankar YD.
Eur. J. Org. Chem.
2002,
1479
16b Baumberger F.
Vasella AI.
Helv. Chim. Acta
1983,
66:
2210
16c Tokunaga Y.
Ihara M.
Fukumoto K.
17a Yang G.
Franck RW.
Bittman R.
Samadder P.
Arthur G.
Org. Lett.
2001,
3:
197
17b Burkhart F.
Hoffmann M.
Kessler H.
Angew.
Chem. Int. Ed.
1997,
36:
1191
17c Roe BA.
Bogamra CG.
Griggs JL.
Bertozzi CR.
J.
Org. Chem.
1996,
61:
6442
17d Montreuil J.
Adv.
Carbohydr. Chem. Biochem.
1980,
37:
157
17e Kornfeld R.
Kornfeld S.
Annu. Rev. Biochem.
1976,
45:
217
18a Zou W.
Wu A.-T.
Bhasin M.
Sandbhor M.
Wu S.-H.
J. Org. Chem.
2007,
72:
2686
18b Wurz RP.
Charette AB.
J.
Org. Chem.
2004,
69:
1262 ;
and references cited therein
18c Solé D.
Bonjoch J.
García-Rubio S.
Peidró E.
Bosch J.
Angew. Chem. Int. Ed.
1999,
38:
395
