Access to L- and D-Iminosugar C-Glycosides from a D-gluco-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy

被引：42

作者：

Mondon, Martine ^{[1
]}

Fontelle, Nathalie ^{[1
]}

Desire, Jerome ^{[1
]}

Lecornue, Frederic ^{[1
]}

Guillard, Jerome ^{[1
]}

Marrot, Jerome ^{[2
]}

Bleriot, Yves ^{[1
]}

机构：

[1] Univ Poitiers, CNRS, Equipe Chim Organ Bioorgan & Supramol, Inst Chim Milieux & Mat Poitiers IC2MP,UMR 7285, F-86022 Poitiers, France

[2] Univ Versailles, CNRS, Inst Lavoisier Versailles, UMR 8180, F-78035 Versailles, France

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 03期

关键词：

NUCLEOPHILIC 1,2-ADDITION; ORGANOMETALLIC REAGENTS; ASYMMETRIC-SYNTHESIS; 1ST SYNTHESIS; FUCOSIDASE; INHIBITION; CHEMISTRY; BINDING; AMINES;

D O I：

10.1021/ol203385w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A flexible synthetic access to six-membered and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.

引用

页码：870 / 873

页数：4

共 42 条

[1] An Oxidation and Ring Contraction Approach to the Synthesis of (±)-1-Deoxynojirimycin and (±)-1-Deoxyaltronojirimycin [J].

Bagal, Sharan K. ;

Davies, Stephen G. ;

Lee, James A. ;

Roberts, Paul M. ;

Russell, Angela J. ;

Scott, Philip M. ;

Thomson, James E. .

ORGANIC LETTERS, 2010, 12 (01) :136-139

[2] Inhibition of fucosyl transferase and fucosidase by a rigid bicyclic mimic of α-L-fucose [J].

Beacham, AR ;

Smelt, KH ;

Biggadike, K ;

Britten, CJ ;

Hackett, L ;

Winchester, BG ;

Nash, RJ ;

Griffiths, RC ;

Fleet, GWJ .

TETRAHEDRON LETTERS, 1998, 39 (1-2) :151-154

[3] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[4] Synthesis and conformational studies by peptidomimetics containing furanoid sugar amino acids an a sugar diacid [J].

Chakraborty, TK ;

Ghosh, S ;

Jayaprakash, S ;

Sharma, JARP ;

Ravikanth, V ;

Diwan, PV ;

Nagaraj, R ;

Kunwar, AC .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6441-6457

[5]

Compain P., 2007, Iminosugars: From Synthesis to Therapeutic Applications, DOI DOI 10.1002/9780470517437.CH1

[6] Tactics and strategies for the synthesis of iminosugar C-glycosides: a review [J].

Compain, Philippe ;

Chagnault, Vincent ;

Martin, Olivier R. .

TETRAHEDRON-ASYMMETRY, 2009, 20 (6-8) :672-711

[7] Practical asymmetric synthesis of 1,2-diamines in the 3-aminoazepane series [J].

Cutri, S ;

Bonin, M ;

Micouin, L ;

Husson, HP ;

Chiaroni, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2645-2651

[8] Glycomimetics at the Mirror: Medicinal Chemistry of L-Iminosugars [J].

D'Alonzo, Daniele ;

Guaragna, Annalisa ;

Palumbo, Giovanni .

CURRENT MEDICINAL CHEMISTRY, 2009, 16 (04) :473-505

[9] Novel cyclic sugar imines: Carbohydrate mimics and easily elaborated scaffolds for aza-sugars [J].

Davis, BG ;

Maughan, MAT ;

Chapman, TM ;

Villard, R ;

Courtney, S .

ORGANIC LETTERS, 2002, 4 (01) :103-106

[10] Synthesis of optically active substituted 3-fluoropiperidines from prolinols by using DAST [J].

Dechamps, Ingrid ;

Gomez Pardo, Domingo ;

Cossy, Janine .

SYNLETT, 2007, (02) :263-267

← 1 2 3 4 5 →