Efficient synthesis of seven-membered iminocyclitols from glycosylenamines.

被引：18

作者：

Fuentes, J ^{[1
]}

Olano, D ^{[1
]}

Pradera, MA ^{[1
]}

机构：

[1] Univ Sevilla, Dept Quim Organ, Fac Quim, E-41071 Seville, Spain

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(99)00649-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Seven membered iminocyclitols are synthesized in four steps from easily available glycosylenamines (D-gluco, D-galacto, and D-manno configurations) through 1,6-aza-anhydrosugar derivatives. These intermediates are transformed into 2-hydroxy- and 2-unsubstituted azepanes depending on the reactants used for the cleavage of the C1-O bond. The overall yields are high. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4063 / 4066

页数：4

共 32 条

[1] A FACILE, PRACTICAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL (MDL 25,637) [J].

ANZEVENO, PB ;

CREEMER, LJ ;

DANIEL, JK ;

KING, CHR ;

LIU, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2539-2542

[2] Aza-C-disaccharides: Synthesis of 6-deoxygalactonojirimycin beta-C(1->3) linked with D-altrofuranosides and D-galactose [J].

Baudat, A ;

Vogel, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6252-6260

[3] C-3- and C-4-alkylated polyhydroxypyrrolidines: Enantiospecific syntheses and glycosidase inhibitory activity [J].

Blanco, MJ ;

Sardina, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3411-3416

[4] PYRROLIDINE AND HEXAHYDRO-1H-AZEPINE MIMICS OF THE FLAP UP MANNOSYL CATION [J].

FARR, RA ;

HOLLAND, AK ;

HUBER, EW ;

PEET, NP ;

WEINTRAUB, PM .

TETRAHEDRON, 1994, 50 (04) :1033-1044

[5] Stereoselective syntheses of 4-amino-aldoses, and chiral pyrrolidine derivatives from glycosylenamines [J].

Fuentes, J ;

Olano, D ;

Pradera, MA .

TETRAHEDRON-ASYMMETRY, 1997, 8 (20) :3443-3456

[6] Stereoselective synthesis of nucleoside analogues of chiral imidazolidines from sugar isothiocyanates [J].

Fuentes, J ;

Molina, JL ;

Olano, D ;

Pradera, MA .

TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :203-218

[7] Biological activities of the nortropane alkaloid, calystegine B-2, and analogs: Structure-function relationships [J].

Goldmann, A ;

Message, B ;

Tepfer, D ;

Molyneux, RJ ;

Duclos, O ;

Boyer, FD ;

Pan, YT ;

Elbein, AD .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (12) :1137-1142

[8]

Gomez Sanchez A, 1984, CARBOHYD RES, V135, P101

[9] SUGAR LACTAMS .3. SYNTHESIS OF 5- 6- AND 7-MEMBERED ANALOGS [J].

HANESSIAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03) :675-+

[10] Synthesis of the first 1-azaanalogues of L-sugars. [J].

Hansen, A ;

Tagmose, TM ;

Bols, M .

TETRAHEDRON, 1997, 53 (02) :697-706

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