Asymmetric dihydroxylation of D-glucose derived α,β-unsaturated ester:: Synthesis of azepane and nojirimycin analogues

被引：78

作者：

Dhavale, DD ^{[1
]}

Markad, SD

Karanjule, NS

PrakashaReddy, J

机构：

[1] Univ Poona, Dept Chem, Garware Res Ctr, Pune 411007, Maharashtra, India

[2] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 14期

关键词：

D O I：

10.1021/jo049509t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric dihydroxylation of a D-glucose derived a,P-unsaturated ester 3 afforded syn vicinal diols in good to high diastereoselectivity. The conversion of these vicinal diols to the corresponding cyclic sulfate, regio-, stereoselective nucleophilic ring opening by sodium azide, and LAH reduction afforded amino heptitols 7a,b that were converted to azepane 1c,d and nojirimycin analogues 2c,d.

引用

页码：4760 / 4766

页数：7

共 68 条

[1] Sharpless asymmetric dihydroxylation on an industrial scale [J].

Ahrgren, L ;

Sutin, L .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1997, 1 (06) :425-427

[2] TOTAL SYNTHESES OF GALACTOSIDASE INHIBITORS (+)-GALACTOSTATIN AND (+)-1-DEOXYGALACTOSTATIN [J].

AOYAGI, S ;

FUJIMAKI, S ;

YAMAZAKI, N ;

KIBAYASHI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :815-819

[3] Novel α-L-fucosidase inhibitors from the bark of Angylocalyx pynaertii (Leguminosae) [J].

Asano, N ;

Yasuda, K ;

Kizu, H ;

Kato, A ;

Fan, JQ ;

Nash, RJ ;

Fleet, GWJ ;

Molyneux, RJ .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 2001, 268 (01) :35-41

[4] Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis [J].

Asano, N ;

Kato, A ;

Miyauchi, M ;

Kizu, H ;

Kameda, Y ;

Watson, AA ;

Nash, RJ ;

Fleet, GWJ .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05) :625-628

[5] Iminosugars from α,β-epoxyamides.: Part 2:: Synthetic approach to hydroxylated pyrrolidine and azepane derivatives [J].

Assiego, C ;

Pino-González, MS ;

López-Herrera, FJ .

TETRAHEDRON LETTERS, 2004, 45 (12) :2611-2613

[6] Double reductive amination of L-arabino-hexos-5-uloses: A diastereoselective approach to 1-deoxy-D-galactostatin derivatives [J].

Barili, PL ;

Berti, G ;

Catelani, G ;

DAndrea, F ;

DeRensis, F ;

Puccioni, L .

TETRAHEDRON, 1997, 53 (09) :3407-3416

[7] trans-1,2-diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: Applications in asymmetric synthesis and molecular recognition [J].

Bennani, YL ;

Hanessian, S .

CHEMICAL REVIEWS, 1997, 97 (08) :3161-3195

[8] A new coupled catalytic system for dihydroxylation of olefins by H2O2 [J].

Bergstad, K ;

Jonsson, SY ;

Bäckvall, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) :10424-10425

[9] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[10] THE SYNTHESIS OF SOME 7-CARBON SUGARS VIA THE OSMYLATION OF OLEFINIC SUGARS [J].

BRIMACOMBE, JS ;

KABIR, AKMS .

CARBOHYDRATE RESEARCH, 1986, 150 (01) :35-51

← 1 2 3 4 5 6 7 →