Iodoacetoxylation of glycals using cerium(IV) ammonium nitrate, sodium iodide, and acetic acid:: Stereoselective synthesis of 2-deoxy-2-iodo-α-mannopyranosyl acetates

被引：33

作者：

Roush, WR ^{[1
]}

Narayan, S ^{[1
]}

Bennett, CE ^{[1
]}

Briner, K ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 06期

关键词：

D O I：

10.1021/ol990815g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The reactions of glycals with ceric(IV) ammonium nitrate and sodium iodide in the presence of acetic acid provides 2-deoxy-2-iodo-alpha- mannopyranosyl acetates with goad stereoselectivity, In the majority of the cases examined, the selectivity was considerably better than that from reactions using N-iodosuccinimide and HOAc.

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收藏

页码：895 / 897

页数：3

相关论文

共 17 条

[1] GLYCOSYLPHOSPHONATES OF 2-AMINO-2-DEOXY-ALDOSES - SYNTHESIS OF A PHOSPHONATE ANALOG OF LIPID X [J].

BRINER, K ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1987, 70 (05) :1341-1356

[2] Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence [J].

Danishefsky, SJ ;

Bilodeau, MT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1380-1419

[3]

DINER UE, 1970, CHEM COMMUN, P333

[4] ON THE CONTROLLED OXIDATIVE COUPLING OF GLYCALS - A NEW STRATEGY FOR THE RAPID ASSEMBLY OF OLIGOSACCHARIDES [J].

FRIESEN, RW ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6656-6660

[5] A NEW ALKOXYIODINATION AND NITRATOIODINATION OF OLEFINS USING IODINE-CERIUM(IV) AMMONIUM-NITRATE [J].

HORIUCHI, CA ;

NISHIO, Y ;

GONG, D ;

FUJISAKI, T ;

KIJI, S .

CHEMISTRY LETTERS, 1991, (04) :607-610

[6]

HORIUCHI CA, 1996, J CHEM RES SYNOP, P60

[7] Phosphonium salts of diacetoxyiodine(I) anions, new reagents for the iodoacetoxylation of alkenes [J].

Kirschning, A ;

Plumeier, C ;

Rose, L .

CHEMICAL COMMUNICATIONS, 1998, (01) :33-34

[8] AZIDONITRATION OF TRI-O-ACETYL-D-GALACTAL [J].

LEMIEUX, RU ;

RATCLIFFE, RM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (10) :1244-1251

[9] The addition of malonates to glycals: A general and convenient method for the synthesis of 2-C-branched carbohydrates [J].

Linker, T ;

Sommermann, T ;

Kahlenberg, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) :9377-9384

[10]

LOWN JW, 1977, CAN J CHEM, V55, P122, DOI 10.1139/v77-022