A SHORT SYNTHESIS OF L-FUCOSE AND ANALOGS FROM D-MANNOSE

被引：15

作者：

GESSON, JP

JACQUESY, JC

MONDON, M

PETIT, P

机构：

[1] Laboratoire de Chimie 12, associé au CNRS, 86022 Poitiers, 40, Avenue du Recteur Pineau

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(00)92522-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient synthesis of L-fucose (and 6-alkyl analogs) in only six steps from D-mannose is described. This transformation is based on addition of an organometallic reagent to the bis-acetonide of D-mannose followed by selective glycol cleavage with sodium periodate Efficient separation of diastereomeric dibenzoates and formation of 2,5-di-O-benzyl(or benzoyl)-L-fucofuranose derivatives are also noteworthy.

引用

页码：3637 / 3640

页数：4

共 18 条

[1] SYNTHESIS OF L-FUCOSE [J].

AKIYA, S ;

SUZUKI, S .

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1954, 74 (12) :1296-1298

[2] A FACILE SYNTHESIS OF 2.4-DI-O-BENZYL-L-FUCOSE FROM D-GLUCOSE [J].

AQEEL, A ;

SATO, K ;

HASHIMOTO, H ;

YOSHIMURA, J .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (03) :405-412

[3]

ARCAMONE F, 1981, DOXORUBICIN ANTICANC, P300

[4] C-NUCLEOSIDE STUDIES .3. GLYCOFURANOSYLETHYNES FROM 2,3-5,6-DI-O-ISOPROPYLIDENE-D-MANNOSE [J].

BUCHANAN, JG ;

DUNN, AD ;

EDGAR, AR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (01) :68-75

[5]

CHIBA T, 1979, CHEM PHARM BULL, V27, P2838

[6]

COREY EJ, 1982, J AM CHEM SOC, V104, P6818, DOI 10.1021/ja00388a074

[7] AN EFFICIENT SYNTHESIS OF L-FUCOSE AND L-(4-H-2)FUCOSE [J].

DEFAYE, J ;

GADELLE, A ;

ANGYAL, SJ .

CARBOHYDRATE RESEARCH, 1984, 126 (01) :165-169

[8]

DEFAYE J, 1981, CARBOHYD RES, V95, P131

[9] SYNTHESIS OF L-FUCOSE [J].

DEJTERJU.M ;

FLOWERS, HM .

CARBOHYDRATE RESEARCH, 1973, 28 (01) :144-146

[10]

Flowers H M, 1981, Adv Carbohydr Chem Biochem, V39, P279

← 1 2 →