Imino-C-nucleoside synthesis:: Heteroaryl lithium carbanion additions to a carbohydrate cyclic imine and nitrone

被引：34

作者：

Evans, GB

Furneaux, RH

Hausler, H

Larsen, JS

Tyler, PC

机构：

[1] Ind Res Ltd, Carbohydrate Chem, Lower Hutt, New Zealand

[2] Graz Tech Univ, Inst Organ Chem, Glycogrp, A-8010 Graz, Austria

[3] Univ So Denmark, Dept Chem, Odense, Denmark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 06期

关键词：

D O I：

10.1021/jo035744k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Promotion by Lewis acid of the addition of some aryllithiums to a carbohydrate-based imine, which has allowed a more facile synthesis of some imino-C-nucleoside analogues, is described. Use of the corresponding nitrone does not assist in some cases, but lithiated acetonitrile adds to it efficiently to give a product from which further C-nucleoside analogues can be derived.

引用

收藏

页码：2217 / 2220

页数：4

相关论文

共 12 条

[1] Comparison of in vivo efficacy of BCX-1777 and cyclosporin in xenogeneic graft-vs.-host disease: the role of dGTP in antiproliferative action of BCX-1777 [J].

Bantia, S ;

Miller, PJ ;

Parker, CD ;

Ananth, SL ;

Horn, LL ;

Babu, YS ;

Sandhu, JS .

INTERNATIONAL IMMUNOPHARMACOLOGY, 2002, 2 (07) :913-923

[2] Purine nucleoside phosphorylase inhibitor BCX-1777 (immucillin-H) - a novel potent and orally active immunosuppressive agent [J].

Bantia, S ;

Miller, PJ ;

Parker, CD ;

Ananth, SL ;

Horn, LL ;

Kilpatrick, JM ;

Morris, PE ;

Hutchison, TL ;

Montgomery, JA ;

Sandhu, JS .

INTERNATIONAL IMMUNOPHARMACOLOGY, 2001, 1 (06) :1199-1210

[3] 8-aza-immucillins as transition-state analogue inhibitors of purine nucleoside phosphorylase and nucleoside hydrolases [J].

Evans, GB ;

Furneaux, RH ;

Gainsford, GJ ;

Hanson, JC ;

Kicska, GA ;

Sauve, AA ;

Schramm, VL ;

Tyler, PC .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (01) :155-160

[4] Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine:: Convergent synthesis of the aza-C-nucleoside immucillins [J].

Evans, GB ;

Furneaux, RH ;

Hutchison, TL ;

Kezar, HS ;

Morris, PE ;

Schramm, VL ;

Tyler, PC .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5723-5730

[5] Synthesis of transition state analogue inhibitors for purine nucleoside phosphorylase and N-riboside hydrolases [J].

Evans, GB ;

Furneaux, RH ;

Gainsford, GJ ;

Schramm, VL ;

Tyler, PC .

TETRAHEDRON, 2000, 56 (19) :3053-3062

[6] PREPARATIONS OF SECONDARY-AMINES AND BETA-AMINO ESTERS VIA ADDITIONS OF GRIGNARD AND REFORMATSKY REAGENTS TO IMINES AND BY ONE-POT REACTIONS OF PRIMARY AMINES, ALDEHYDES, AND GRIGNARDS [J].

KATRITZKY, AR ;

HONG, QM ;

YANG, ZJ .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3405-3408

[7] Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes [J].

Kicska, GA ;

Long, L ;

Hörig, H ;

Fairchild, C ;

Tyler, PC ;

Furneaux, RH ;

Schramm, VL ;

Kaufman, HL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (08) :4593-4598

[8] One-third-the-sites transition-state inhibitors for purine nucleoside phosphorylase [J].

Miles, RW ;

Tyler, PC ;

Furneaux, RH ;

Bagdassarian, CK ;

Schramm, VL .

BIOCHEMISTRY, 1998, 37 (24) :8615-8621

[9]

Schreiber S. L, 1991, COMPREHENSIVE ORGANI, V1

[10] PYRAZOLO[4,3-D]PYRIMIDINES - REGIOSELECTIVITY OF N-ALKYLATION - FORMATION, REARRANGEMENT, AND ALDEHYDE COUPLING REACTIONS OF 3-LITHIO DERIVATIVES [J].

STONE, TE ;

EUSTACE, EJ ;

PICKERING, MV ;

DAVES, GD .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (04) :505-509