Sucrose tricarboxylate by sonocatalysed TEMPO-mediated oxidation

被引：41

作者：

Lemoine, S ^{[1
]}

Thomazeau, C ^{[1
]}

Joannard, D ^{[1
]}

Trombotto, S ^{[1
]}

Descotes, G ^{[1
]}

Bouchu, A ^{[1
]}

Queneau, Y ^{[1
]}

机构：

[1] Eridania Beghin Say CEI, UMR 143, CNRS Beghin Say, Unite Mixte Sucrochim, F-69603 Villeurbanne, France

来源：

CARBOHYDRATE RESEARCH | 2000年 / 326卷 / 03期

关键词：

sucrose; oxidation; ultrasound; TEMPO; uronic acids;

D O I：

10.1016/S0008-6215(00)00046-X

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：

Oxidation of sucrose by the NaOCl/TEMPO system provided sucrose tricarboxylate without the addition of sodium bromide as co-catalyst when high-frequency (500 kHz) ultrasound was applied, in contrast to very limited conversion without sonication. In the presence of sodium bromide, sonication also caused acceleration of the oxidation. The rate increase due to sonication of the oxidant system prior to sucrose addition suggests that ultrasound acts at the level of the formation of the nitrosonium ion, the active oxidising species in the catalytic cycle. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：176 / 184

页数：9

共 36 条

[1]

ANELLI PL, 1987, J ORG CHEM, V52, P2559

[2]

Bekkum H. van, 1994, Proceedings of the SPRI Workshop on products of sugarbeet and sugarcane, Helsinki, Finland, 10-11 August 1994., P264

[3] THE CATALYTIC EFFECT OF BROMIDE IN THE HYPOCHLORITE OXIDATION OF LINEAR DEXTRINS AND INULIN [J].

BESEMER, AC ;

VANBEKKUM, H .

STARCH-STARKE, 1994, 46 (03) :101-106

[4] DICARBOXY-STARCH BY SODIUM-HYPOCHLORITE BROMIDE OXIDATION AND ITS CALCIUM-BINDING PROPERTIES [J].

BESEMER, AC ;

VANBEKKUM, H .

STARCH-STARKE, 1994, 46 (03) :95-101

[5] Effect of ultrasound on KSF/O mediated glycosylations [J].

Brochette, S ;

Descotes, G ;

Bouchu, A ;

Queneau, Y ;

Monnier, N ;

Petrier, C .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 123 (2-3) :123-130

[6] Ultrasound promoted glucose oligomerization under Fischer glycosylation conditions: Structural aspects [J].

Brochette, S ;

Descotes, G ;

Bouchu, A ;

Queneau, Y ;

Lemoine, J .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1998, 17 (06) :879-891

[7] Sonocatalysis of the TEMPO-mediated oxidation of glucosides [J].

Brochette-Lemoine, S ;

Joannard, D ;

Descotes, G ;

Bouchu, A ;

Queneau, Y .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 150 (1-2) :31-36

[8] NITROXIDE-CATALYZED OXIDATION OF ALCOHOLS USING META-CHLOROPERBENZOIC ACID - NEW METHOD [J].

CELLA, JA ;

KELLEY, JA ;

KENEHAN, EF .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (12) :1860-1862

[9] SELECTIVE OXIDATION OF MONOSACCHARIDE DERIVATIVES TO URONIC-ACIDS [J].

DAVIS, NJ ;

FLITSCH, SL .

TETRAHEDRON LETTERS, 1993, 34 (07) :1181-1184

[10]

deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153

← 1 2 3 4 →