Lithium tetrafluoborate catalyzed Ferrier rearrangement - Facile synthesis of alkyl 2,3-unsaturated glycopyranosides

被引：22

作者：

Babu, BS ^{[1
]}

Balasubramanian, KK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Chennai, India

来源：

SYNTHETIC COMMUNICATIONS | 1999年 / 29卷 / 24期

关键词：

D O I：

10.1080/00397919908086589

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of tri-O acetyl-D-galactal 1 and tri-O-acetyl-D-glucal 2 with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl 2,3-unsaturated glycopyranosides 3-18 (50-86%).

引用

页码：4299 / 4305

页数：7

共 18 条

[1] Mild and efficient tetrahydropyranylation of alcohols-catalysis by lithium percholorate in diethyl ether. [J].

Babu, BS ;

Balasubramanian, KK .

TETRAHEDRON LETTERS, 1998, 39 (50) :9287-9288

[2]

BABU BS, 1998, 215 AM CHEM SOC NAT

[3] STUDIES ON LACTAMS .96. STEREOSPECIFIC GLYCOSYLATION VIA FERRIER REARRANGEMENT FOR OPTICAL RESOLUTION [J].

BANIK, BK ;

MANHAS, MS ;

BOSE, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4714-4716

[4] ALLYLIC REARRANGEMENT OF 6-DEOXYGLYCALS HAVING PRACTICAL UTILITY [J].

BHATE, P ;

HORTON, D ;

PRIEBE, W .

CARBOHYDRATE RESEARCH, 1985, 144 (02) :331-337

[5] A SIMPLE DIASTEREOSELECTIVE SYNTHESIS OF 2',3'-UNSATURATED ARYL C-GLUCOPYRANOSIDES [J].

CASIRAGHI, G ;

CORNIA, M ;

RASSU, G ;

ZETTA, L ;

FAVA, GG ;

BELICCHI, MF .

TETRAHEDRON LETTERS, 1988, 29 (27) :3323-3326

[6]

Ferrier R J, 1969, Adv Carbohydr Chem Biochem, V24, P199

[7] UNSATURATED CARBOHYDRATES .9. SYNTHESIS OF 2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDES FROM TRI-O-ACETYL-D-GLUCAL [J].

FERRIER, RJ ;

PRASAD, N .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04) :570-&

[8] SOME PROGENY OF 2,3-UNSATURATED SUGARS - THEY LITTLE RESEMBLE GRANDFATHER GLUCOSE - 10 YEARS LATER [J].

FRASERREID, B .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (11) :347-354

[9]

GRIECO PA, 1991, J AM CHEM SOC, P113

[10] SYNTHESIS OF ALKYL 4,6-DI-O-ACETYL-2,3-DIDEOXY-ALPHA-D-THREO-HEX-2-ENOPYRANOSIDES FROM 3,4,6-TRI-O-ACETYL-1,5-ANHYDRO-2-DEOXY-D-LYXO-HEX-1-ENITOL (3,4,6-TRI-O-ACETYL-D-GALACTAL) [J].

GRYNKIEWICZ, G ;

PRIEBE, W ;

ZAMOJSKI, A .

CARBOHYDRATE RESEARCH, 1979, 68 (01) :33-41

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