Silver(I)-catalyzed addition of zirconocenes to glycal epoxides.: A new synthesis of α-C-glycosides

被引：27

作者：

Wipf, P ^{[1
]}

Pierce, JG

Zhuang, N

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[2] Univ Pittsburgh, Ctr Chem Methodol & Library Dev, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 03期

关键词：

D O I：

10.1021/ol0475414

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrozirconation of terminal alkynes, followed by AgClO4-catalyzed in situ addition of the resultant alkenylzirconocenes to 1,2-anhydrosugars (glycal epoxides) leads to alpha-C-glycosides in moderate to high yields.

引用

页码：483 / 485

页数：3

共 43 条

[1] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].

ADAM, W ;

BIALAS, J ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377

[2] C-glycosides to fused polycyclic ethers [J].

Allwein, SP ;

Cox, JM ;

Howard, BE ;

Johnson, HWB ;

Rainier, JD .

TETRAHEDRON, 2002, 58 (10) :1997-2009

[3]

Bailey JM, 1999, SYNLETT, P132

[4] STEREOCONTROLLED SYNTHESIS OF C-GLYCOSIDES BY REACTION OF ORGANOCUPRATES WITH PROTECTED 1,2-ANHYDRO SUGARS, AND THEIR TRANSFORMATION INTO 2-DEOXY-C-GLYCOSIDES [J].

BELLOSTA, V ;

CZERNECKI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (03) :199-200

[5] Sc(OTf)3 as efficient catalyst for aryl C-glycoside synthesis [J].

Ben, A ;

Yamauchi, T ;

Matsumoto, T ;

Suzuki, K .

SYNLETT, 2004, (02) :225-230

[6] The synthesis of some epoxyalkyl beta-C-glycosides as potential inhibitors of beta-glucan hydrolases [J].

Best, WM ;

Ferro, V ;

Harle, J ;

Stick, RV ;

Tilbrook, DMG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (05) :463-472

[7]

BHAGWATHEESWARAN H, 1976, SYNTHESIS-STUTTGART, P615

[8] Synthesis of L-sugars from 4-deoxypentenosides [J].

Boulineau, FP ;

Wei, A .

ORGANIC LETTERS, 2002, 4 (13) :2281-2283

[9] A novel approach to the stereocontrolled synthesis of C-vinyl β-D-galactopyranosides [J].

Caputo, R ;

Festa, P ;

Guaragna, A ;

Palumbo, G ;

Pedatella, S .

CARBOHYDRATE RESEARCH, 2003, 338 (18) :1877-1880

[10] SYNTHESIS OF (+/-)-CP-99,994 - A HIGHLY POTENT SUBSTANCE-P ANTAGONIST [J].

DESAI, MC ;

THADEIO, PF ;

LEFKOWITZ, SL .

TETRAHEDRON LETTERS, 1993, 34 (37) :5831-5834

← 1 2 3 4 5 →