Synthesis in water of amphiphilic sucrose hydroxyalkyl ethers

被引：32

作者：

Gagnaire, J ^{[1
]}

Toraman, G ^{[1
]}

Descotes, G ^{[1
]}

Bouchu, A ^{[1
]}

Queneau, Y ^{[1
]}

机构：

[1] CEI, Eridania Beghin Say, CNRS, UMR 143 Sucrochim, F-69609 Villeurbanne, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 14期

关键词：

surfactants; carbohydrates; etherification; epoxide;

D O I：

10.1016/S0040-4039(99)00321-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the preparation of amphiphilic hydroxyalkylsucrose ethers from unprotected sucrose in water and we show that among the monosubstituted products, the 2- and 1'- regioisomers account for 60% of the mixture. The high reactivity of these positions is thus confirmed in water as it is in dipolar aprotic solvents. A careful analysis also show evidence of the formation of oligomerisation products as by-products. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2757 / 2760

页数：4

共 28 条

[1]

Anderson A.W., 1959, inventor

[2]

The Dow Chemical Co., assignee, Patent No. [US2902478, 2902478]

[3] THE CONFORMATIONAL PROPERTIES OF SUCROSE IN AQUEOUS-SOLUTION - INTRAMOLECULAR HYDROGEN-BONDING [J].

BOCK, K ;

LEMIEUX, RU .

CARBOHYDRATE RESEARCH, 1982, 100 (MAR) :63-74

[4] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES [J].

BOCK, K ;

PEDERSEN, C .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 :27-66

[5]

Bunton CA., 1987, ADV PHYS ORG CHEM, V22, P213, DOI [10.1016/S0065-3160(08)60169-0, DOI 10.1016/S0065-3160(08)60169-0]

[6] CO-OPERATIVE AND COMPETITIVE HYDROGEN-BONDING IN SUCROSE DETERMINED BY SIMPLE-H-1 NMR-SPECTROSCOPY [J].

CHRISTOFIDES, JC ;

DAVIES, DB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (21) :1533-1534

[7]

CRECELIUS SB, 1962, Patent No. 3018281

[8]

Descotes G., 1993, CARBOHYDRATES ORGANI

[9]

du Penhoat CH, 1997, CARBOHYD RES, V305, P131, DOI 10.1016/S0008-6215(97)00258-9

[10] MOLECULAR RELAXATION OF SUCROSE IN AQUEOUS-SOLUTION - HOW A NANOSECOND MOLECULAR-DYNAMICS SIMULATION HELPS TO RECONCILE NMR DATA [J].

ENGELSEN, SB ;

DUPENHOAT, CH ;

PEREZ, S .

JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (36) :13334-13351

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