Total Synthesis of Nucleoside Antibiotics Possessing Novel N-Glycoside Structures

被引：7

作者：

Chida, Noritaka ^{[1
]}

机构：

[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2008年 / 66卷 / 11期

关键词：

D O I：

10.5059/yukigoseikyokaishi.66.1105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Construction of aryl and heteroaryl N-glycoside structures by way of the palladium-catalyzed Buchwald-Hartwig N-arylation of pyranosylamines with aryl and heteroaryl halide derivatives is described. This methodology was successfully applied to the total synthesis of nucleoside antibiotics, spicamycin and dapiramicin B, possessing novel heteroaryl N-glycosides. Kinetic and thermodynamic analyses of heteroaryl N-glycosides are also reported.

引用

页码：1105 / 1115

页数：11

共 88 条

[1]

ABRAMOVITCH RA, 1971, CHEM AZIDO GROUP, pCH5

[2] ANTI-TUMOR SEPTACIDIN ANALOGS [J].

ACTON, EM ;

RYAN, KJ ;

LUETZOW, AE .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (11) :1362-1371

[3] NOVEL DISACCHARIDES CONTAINING SULFUR IN THE RING AND NITROGEN IN THE INTERGLYCOSIDIC LINKAGE - CONFORMATION OF METHYL 5'-THIO-4-N-ALPHA-MALTOSIDE BOUND TO GLUCOAMYLASE AND ITS ACTIVITY AS A COMPETITIVE INHIBITOR [J].

ANDREWS, JS ;

WEIMAR, T ;

FRANDSEN, TP ;

SVENSSON, B ;

PINTO, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :10799-10804

[4]

[Anonymous], 1993, The inositol phosphates: chemical synthesis and biological significance

[5]

[Anonymous], 1993, ANOMERIC EFFECT ASS

[6] RECENT DEVELOPMENTS IN THE SYNTHESIS OF MYOINOSITOL PHOSPHATES [J].

BILLINGTON, DC .

CHEMICAL SOCIETY REVIEWS, 1989, 18 (01) :83-122

[7] Natural products to drugs: natural product-derived compounds in clinical trials [J].

Butler, Mark S. .

NATURAL PRODUCT REPORTS, 2008, 25 (03) :475-516

[8] Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines:: Synthesis of 6-(β-D-mannopyranosylamino)-9H-purine and its β-D-gluco isomer, N-glycoside models for spicamycin and septacidin [J].

Chida, N ;

Suzuki, T ;

Tanaka, S ;

Yamada, I .

TETRAHEDRON LETTERS, 1999, 40 (13) :2573-2576

[9] SYNTHESIS OF METHYL (METHYL D-IDOPYRANOSID AND L-IDOPYRANOSID)URONATES - FROM MYOINOSITOL [J].

CHIDA, N ;

YAMADA, E ;

OGAWA, S .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (03) :555-570

[10] Synthesis of acyclic and heterocyclic natural products utilizing cyclitols as novel chiral building blocks [J].

Chida, N ;

Ogawa, S .

CHEMICAL COMMUNICATIONS, 1997, (09) :807-813

← 1 2 3 4 5 6 7 8 9 →