SYNTHESIS OF ALPHA-METHYL 1',2'-DIDEOXYCELLOBIOSIDE - A NOVEL C-DISACCHARIDE

被引：38

作者：

ARMSTRONG, RW

TEEGARDEN, BR

机构：

[1] Department of Chemistry and Biochemistry, University of California, Los Angeles

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 03期

关键词：

D O I：

10.1021/jo00029a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bromonium ion induced 6-endo-trig cyclizations of E olefine derived from D-arabinose provide a stereoselective route to 2'-deoxyglucono-beta-C-glycosides. Use of delta-alkenols containing allylic isopropylidenes (i.e., 1) prevents formation of furan products due to the highly strained transition state necessary for formation of the trans [3.3.0] bicyclic systems. Because the exo-anomeric carbon is not involved in the cyclization, previously established stereocenters at this carbon are left intact. Application of this methodology to the synthesis of alpha-methyl 1',2'-dideoxycellobioside (22) is presented. The restricted rotation about the bond connecting the two sugars affords a unique staggared conformation of the disaccharide.

引用

收藏

页码：915 / 922

页数：8

相关论文

共 32 条

[1] TOTAL SYNTHESIS OF A FULLY PROTECTED PALYTOXIN CARBOXYLIC-ACID [J].

ARMSTRONG, RW ;

BEAU, JM ;

CHEON, SH ;

CHRIST, WJ ;

FUJIOKA, H ;

HAM, WH ;

HAWKINS, LD ;

JIN, H ;

KANG, SH ;

KISHI, Y ;

MARTINELLI, MJ ;

MCWHORTER, WW ;

MIZUNO, M ;

NAKATA, M ;

STUTZ, AE ;

TALAMAS, FX ;

TANIGUCHI, M ;

TINO, JA ;

UEDA, K ;

UENISHI, J ;

WHITE, JB ;

YONAGA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7525-7530

[2] PREFERRED CONFORMATION OF C-GLYCOSIDES .3. PREFERRED CONFORMATION OF CARBON ANALOGS OF 1,4-DISACCHARIDES [J].

BABIRAD, SA ;

WANG, Y ;

GOEKJIAN, PG ;

KISHI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4825-4827

[3] SYNTHESIS OF C-DISACCHARIDES [J].

BABIRAD, SA ;

WANG, Y ;

KISHI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1370-1372

[4] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[5] SYNTHESIS AND ANTIVIRAL ACTIVITY OF 3'-DEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES [J].

BAMFORD, MJ ;

COE, PL ;

WALKER, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2494-2501

[6] TANDEM NUCLEOPHILIC AND RADICAL CHEMISTRY IN THE REPLACEMENT OF THE HYDROXYL GROUP BY A CARBON CARBON BOND - A CONCISE SYNTHESIS OF SHOWDOMYCIN [J].

BARTON, DHR ;

RAMESH, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :891-892

[7] POLYSUBSTITUTED DIHYDROPYRANS VIA THE ENOLATE CLAISEN REARRANGEMENT - A STEREOCONTROLLED ROUTE TO C-PYRANOSIDES [J].

BURKE, SD ;

ARMISTEAD, DM ;

SCHOENEN, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4320-4322

[8] SELECTIVE MONO-CLAISEN REARRANGEMENT OF CARBOHYDRATE GLYCALS - A CHEMICAL CONSEQUENCE OF THE VINYLOGOUS ANOMERIC EFFECT [J].

CURRAN, DP ;

SUH, YG .

CARBOHYDRATE RESEARCH, 1987, 171 :161-191

[9] STEREOSELECTIVE SYNTHESIS OF LINEAR C-DISACCHARIDES [J].

DALY, SM ;

ARMSTRONG, RW .

TETRAHEDRON LETTERS, 1989, 30 (42) :5713-5716

[10] CHELATION-CONTROLLED FACIALLY SELECTIVE CYCLOCONDENSATION REACTIONS OF CHIRAL ALKOXY ALDEHYDES - SYNTHESES OF A MOUSE ANDROGEN AND OF A CARBON-LINKED DISACCHARIDE [J].

DANISHEFSKY, SJ ;

PEARSON, WH ;

HARVEY, DF ;

MARING, CJ ;

SPRINGER, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1256-1268

← 1 2 3 4 →