Hydroxylamine Derivatives as Nucleophiles in Ferrier Glycosylation: Synthesis of Aminoxy Pseudoglycals

Ch. Raji Reddy; Y. Srinivasa Rao; T. Pavan Kumar; K. Venkatram Reddy; S. Chandrasekhar

doi:10.1055/s-2007-1000828

PAPER

Hydroxylamine Derivatives as Nucleophiles in Ferrier Glycosylation: Synthesis of Aminoxy Pseudoglycals [1]

Ch. Raji Reddy*, Y. Srinivasa Rao, T. Pavan Kumar, K. Venkatram Reddy, S. Chandrasekhar
Organic Division - I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: rajireddy@iict.res.in;

Abstract

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Abstract

The use of hydroxylamine derivatives as the aminoxy equivalent nucleophiles in Ferrier glycosylation catalyzed by various acid catalysts is described. The reaction of tri-O-protected d-glucal with N-hydroxyphthalimide or N-hydroxysuccinimide was effectively promoted by a catalytic amount of zinc(II) chloride to produce the corresponding aminoxy pseudoglycal in good yields and preferential anomeric selectivity.

Key words

hydroxylamines - Ferrier glycosylation - pseudoglycals

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References

IICT Communication No. 070126.

<A NAME="RZ17707SS-2A">2a</A> Rodriguez EC. Marcaurelle LA. Bertozzi CR. J. Org. Chem. 1998, 63: 7134

<A NAME="RZ17707SS-2B">2b</A> Marcaurelle LA. Rodriguez EC. Bertozzi CR. Tetrahedron Lett. 1998, 39: 8417

<A NAME="RZ17707SS-2C">2c</A> Rodriguez EC. Winans KA. King DS. Bertozzi CR. J. Am. Chem. Soc. 1997, 119: 9905

<A NAME="RZ17707SS-2D">2d</A> Cooper TS. Larigo AS. Laurent P. Moody CJ. Takle AK. Org. Biomol. Chem. 2005, 3: 1252

<A NAME="RZ17707SS-2E">2e</A> Moody CJ. Chem. Commun. 2004, 1341

<A NAME="RZ17707SS-2F">2f</A> Atobe M. Yamazaki N. Kibayashi C. J. Org. Chem. 2004, 69: 5595

<A NAME="RZ17707SS-2G">2g</A> Hunt JCA. Laurent P. Moody CJ. J. Chem. Soc., Perkin Trans. 1 2002, 2378

<A NAME="RZ17707SS-3">3</A> Cervini SE. Dumy P. Mutter M. Angew. Chem., Int. Ed. Engl. 1996, 35: 1230

<A NAME="RZ17707SS-4">4</A> Li X. Yang D. Chem. Commun. 2006, 3367

<A NAME="RZ17707SS-5">5</A> Renaudet O. Dumy P. Tetrahedron Lett. 2001, 42: 7575

<A NAME="RZ17707SS-6A">6a</A> Fraser-Reid B. Acc. Chem. Res. 1985, 18: 347

<A NAME="RZ17707SS-6B">6b</A> Ferrier RJ. Adv. Carbohydr. Chem. Biochem. 1969, 24: 199

<A NAME="RZ17707SS-6C">6c</A> Dorgan BJ. Jackson RFW. Synlett 1996, 859

<A NAME="RZ17707SS-6D">6d</A> Schmidt RR. Angerbauer R. Angew. Chem., Int. Ed. Engl. 1977, 16: 783

<A NAME="RZ17707SS-6E">6e</A> Schmidt RR. Angerbauer R. Carbohydr. Res. 1979, 72: 272

<A NAME="RZ17707SS-6F">6f</A> Borrachero-Moya P. Cabrera-Escribano F. Gomez-Guillen M. Peredes-Leon MR. Carbohydr. Res. 1998, 308: 181

<A NAME="RZ17707SS-6G">6g</A> Schmidt RR. Angerbauer R. Carbohydr. Res. 1981, 89: 159

<A NAME="RZ17707SS-6H">6h</A> Danishefsky SJ. Bilodeau MT. Angew. Chem., Int. Ed. Engl. 1996, 30: 1357

<A NAME="RZ17707SS-6I">6i</A> Bussolo VD. Kim Y.-J. Gin DY. J. Am. Chem. Soc. 1998, 120: 13515

<A NAME="RZ17707SS-6J">6j</A> Tolstikov AG. Tolstikov GA. Russ. Chem. Rev. 1993, 62: 579

<A NAME="RZ17707SS-7A">7a</A> Ferrier RJ. Prasad N. J. Chem. Soc. C 1969, 1: 570

<A NAME="RZ17707SS-7B">7b</A> For a review on the Ferrier rearrangement, see: Ferrier RJ. Top. Curr. Chem. 2001, 215: 153

<A NAME="RZ17707SS-7C">7c</A> For a review on glycosidation, see: Toshima K. Tatsuta K. Chem. Rev. 1993, 93: 1503

<A NAME="RZ17707SS-8A">8a</A> Takhi M. Abdel-Rahman AA.-H. Schmidt RR. Tetrahedron Lett. 2001, 42: 4053

<A NAME="RZ17707SS-8B">8b</A> Yadav JS. Reddy BVS. Chand PK. Tetrahedron Lett. 2001, 42: 4057

<A NAME="RZ17707SS-8C">8c</A> Yadav JS. Reddy BVS. Raman JV. Niranjan N. Kumar SK. Kunwar AC. Tetrahedron Lett. 2002, 43: 2095

<A NAME="RZ17707SS-8D">8d</A> Das KS. Reddy KA. Abbineni C. Roy J. Rao KVLN. Sachwani RH. Iqbal J. Tetrahedron Lett. 2003, 44: 4507 ; and references cited therein

<A NAME="RZ17707SS-9A">9a</A> Chandrasekhar S. Reddy ChR. Chandrashekar G. Tetrahedron Lett. 2004, 45: 6481

<A NAME="RZ17707SS-9B">9b</A> Yadav JS. Reddy BVS. Synthesis 2002, 511

<A NAME="RZ17707SS-9C">9c</A> Houston TA. Chervin SM. Koreeda M. ITE Lett. Batter. New Technol. Med. 2002, 3: 23

<A NAME="RZ17707SS-9D">9d</A> Kawabata H. Kubo S. Hayashi M. Carbohydr. Res. 2001, 333: 153 ; and references cited therein

<A NAME="RZ17707SS-10A">10a</A> Smitha G. Reddy ChS. Synthesis 2004, 834

<A NAME="RZ17707SS-10B">10b</A> Bettadaiah BK. Srinivas P. Tetrahedron. Lett. 2003, 44: 7257

<A NAME="RZ17707SS-10C">10c</A> Shanmugasundaram B. Bose AK. Balasubramanian KK. Tetrahedron Lett. 2002, 43: 6795

<A NAME="RZ17707SS-10D">10d</A> Swamy NR. Venkateshwarlu Y. Synthesis 2002, 598

<A NAME="RZ17707SS-10E">10e</A> Takhi M. Abdel-Rahman AA.-H. Schmidt RR. Synlett 2001, 427

<A NAME="RZ17707SS-10F">10f</A> Masson C. Soto J. Bessodes M. Synlett 2000, 1281

<A NAME="RZ17707SS-10G">10g</A> Yadav JS. Reddy BVS. Murthy CVSR. Kumar GM. Synlett 2000, 1450

<A NAME="RZ17707SS-10H">10h</A> Babu BS. Balasubramanian KK. Tetrahedron Lett. 1999, 40: 5777

<A NAME="RZ17707SS-11A">11a</A> Yadav JS. Reddy BVS. Geetha V. Synth. Commun. 2003, 33: 717

<A NAME="RZ17707SS-11B">11b</A> Babu BS. Balasubramanian KK. Tetrahedron Lett. 1999, 40: 5777 ; and references cited therein

<A NAME="RZ17707SS-12">12</A> Rajendra M. Srivastava RM. Oliveira FJS. da Silva LP. Filho JRF. Oliveira SP. Lima VLM. Carbohydr. Res. 2001, 332: 335 ; in this report the authors used BF₃·OEt₂ as a catalyst in benzene and observed the formation of only the α-anomer

<A NAME="RZ17707SS-13">13</A> Reddy ChR. Kiranmai N. Kiran Babu GS. Sarma DG. Jagadeesh B. Chandrasekhar S. Tetrahedron Lett. 2007, 48: 215

<A NAME="RZ17707SS-14A">14a</A> Miyabe H. Yoshida K. Yamaguchi M. Takemoto Y. J. Org. Chem. 2005, 70: 2148

<A NAME="RZ17707SS-14B">14b</A> Miyabe H. Matsumura A. Moriyama K. Takemoto Y. Org. Lett. 2004, 6: 4631

<A NAME="RZ17707SS-14C">14c</A> Miyabe H. Yoshida K. Matsumura A. Yamaguchi M. Takemoto Y. Synlett 2003, 567

This product showed hypolipidemic activity in mice, see ref. 12.

<A NAME="RZ17707SS-16">16</A> These types of compounds are useful advanced intermediates for making bio-active molecules, see: Tejler J. Leffler H. Nilsson UJ. Bioorg. Med. Chem. Lett. 2005, 15: 2343

<A NAME="RZ17707SS-17">17</A> For bio-active molecules, see: Thomas M. Rivault F. Tranoy-Opalinski I. Roche J. Gesson J.-P. Papot S. Bioorg. Med. Chem. Lett. 2007, 17: 983