CONVENIENT SYNTHESIS OF MONO AND CYCLIC SULFATES OF CARBOHYDRATES VIA TRIFLATE DISPLACEMENT

被引:11
作者
LATIF, F
SHEKHANI, MS
VOELTER, W
机构
[1] UNIV TUBINGEN,INST PHYSIOL CHEM,PHYS BIOCHEM ABT,HOPPE SEYLER STR 1,W-7400 TUBINGEN 1,GERMANY
[2] UNIV KARACHI,HEJ RES INST CHEM,KARACHI 32,PAKISTAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 06期
关键词
D O I
10.1039/p19900001573
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 2,3-anhydropyranoside-4-triflates (1), (3), and (6) react with tetrabutylammonium hydrogen sulphate to afford the sulphate esters (2), (4), and (7) respectively. In the case of triflates (3) and (6) the cyclic sulphates (5) and (8) were obtained as major products. The benzyl pyranoside (8) was successfully deblocked to yield the free sugar cyclic sulphate (9). The 1H NMR spectra of the newly synthesized sulphates have been discussed in detail. The 13C NMR spectral data are also described.
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收藏
页码:1573 / 1575
页数:3
相关论文
共 32 条
[1]  
AFZA N, 1985, LIEBIGS ANN CHEM, P1929
[2]  
AOI Y, 1981, J MED, V12, P127
[3]   C-13-NMR STUDIES OF D-GLUCOSE AND D-GALACTOSE MONOSULFATES [J].
ARCHBALD, PJ ;
FENN, MD ;
ROY, AB .
CARBOHYDRATE RESEARCH, 1981, 93 (02) :177-190
[4]   THE REACTION OF SULPHURYL CHLORIDE WITH GLYCOSIDES AND SUGAR ALCOHOLS .1. [J].
BRAGG, PD ;
JONES, JKN ;
TURNER, JC .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1959, 37 (09) :1412-1416
[5]   CONFORMATIONAL ANALYSIS OF SOME METHYL 2,3-ANHYDROGLYCOPYRANOSIDES AND 3,4-ANHYDROGLYCOPYRANOSIDES [J].
BUCHANAN, JG ;
FLETCHER, R ;
PARRY, K ;
THOMAS, WA .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (04) :377-&
[6]   STUDIES OF SYNTHESIS AND CONFORMATION IN D-RIBOPYRANOSE SERIES [J].
COXON, B .
TETRAHEDRON, 1966, 22 (07) :2281-&
[7]  
EGAMI F, 1979, GLUCOCONJUGATE RES, P427
[8]   REACTIONS OF SULFUR TRIOXIDE, AND OF ITS ADDUCTS, WITH ORGANIC COMPOUNDS [J].
GILBERT, EE .
CHEMICAL REVIEWS, 1962, 62 (06) :549-&
[9]   Two new derivates of treholose and mannite and an alpha-methyl glucoside-dichlorohydrin. [J].
Helferich, B ;
Lowa, A ;
Nippe, W ;
Riedel, H .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1923, 56 :1083-1087
[10]   Two new derivatives of alpha- and beta-methyl-glucoside. (Preliminary announcement.) [J].
Helferich, B .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1921, 54 :1082-1084