ACTION OF BROMINE ON TETRA-0-ACETYL-1-S-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSE . FORMATION AND DECOMPOSITION OF TETRA-0-ACETYL-BETA-D-GLUCOPYRANOSYLSULFENYL BROMIDE

被引:13
作者
BELL, RH
HORTON, D
机构
[1] Department of Chemistry, The Ohio State University, Columbus
关键词
D O I
10.1016/S0008-6215(00)82134-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Treatment of either tetra-O-acetyl-1-S-acetyl-1-thio-β-D-glucopyranose (1) or tert-butyl tetra-O-acetyl-1-thio-β-D-glucopyranoside (6) with a >3-molar excess of bromine in carbon tetrachloride or pure chloroform, at 10° for 1-3 min, gives tetra-O-acetyl-β-D-glucopyranosylsulfenyl bromide (2) in quantitative yield; prolonged exposure to bromine at room temperature converts the product 2 into tetra-O-acetyl-α-D-glucopyranosyl bromide (3). Slow addition of bromine to the 1-thioglycoside 6 in carbon tetrachloride, or bromination of the thiolacetate 1 in reagent-grade chloroform, gives bis(tetra-O-acetyl-β-D-glucopyranosyl) disulfide (4), also obtainable by treating the sulfenyl bromide 2 with dry ethanol or with the 1-thioglycoside 6. Oxidation of the disulfide 4 with m-chloroperoxybenzoic acid gives a mono-oxide derivative 5, also obtainable by treating the sulfenyl bromide 2 with water or 95% ethanol. The disulfide 4 and its mono-oxide 5 were both converted into the bromide 3 by prolonged exposure to bromine at room temperature. © 1969.
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页码:187 / &
相关论文
共 15 条
[1]   REACTIONS OF TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLSULFENYL BROMIDE [J].
BELL, RH ;
HORTON, D ;
MILLER, MJ .
CARBOHYDRATE RESEARCH, 1969, 9 (02) :201-&
[2]   NUCLEAR MAGNETIC RESONANCE STUDIES ON ACETYLATED 1-THIOALDOPYRANOSE DERIVATIVES [J].
HOLLAND, CV ;
HORTON, D ;
MILLER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (10) :3077-&
[3]  
HOLLAND CV, 1965, 149 AM CHEM SOC M, pD1
[4]   CONFORMATIONAL AND CONFIGURATIONAL STUDIES ON SOME ACETYLATED ALDOPYRANOSYL HALIDES [J].
HORTON, D ;
TURNER, WN .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (10) :3387-&
[5]   THIOSUGARS .1. SYNTHESIS OF DERIVATIVES OF 2-AMINO-2-DEOXY-1-THIO-D-GLUCOSE [J].
HORTON, D ;
WOLFROM, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) :1794-&
[6]   CONVERSION OF 2-AMINO-2-DEOXY-1-THIO-D-GLUCOSE DERIVATIVES INTOGLYCOSYL HALIDE DERIVATIVES - A TETRA-O-ACETYL-GLYCOSYSULFENYL BROMIDE [J].
HORTON, D ;
GRAG, HG ;
WOLFROM, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (11) :2992-&
[7]  
Horton D., 1965, CARBOHYDR RES, V1, P335
[8]  
KHARASCH N, 1967, NOV P INTR S SULF ED
[9]  
KHARASCH N, 1967, Q REP SULFUR CHEM, V2, P289
[10]  
KHARASCH N, 1966, QUART REP SULFUR CHE, V1, P93