THE FORMATION OF ISOPROPYLIDENE ACETALS OF ERYTHRITOL AND RIBITOL UNDER CONDITIONS OF KINETIC CONTROL

被引：5

作者：

AWAL, A ^{[1
]}

BOYD, ASF ^{[1
]}

BUCHANAN, JG ^{[1
]}

EDGAR, AR ^{[1
]}

机构：

[1] HERIOT WATT UNIV,DEPT CHEM,EDINBURGH EH14 4AS,MIDLOTHIAN,SCOTLAND

来源：

CARBOHYDRATE RESEARCH | 1990年 / 205卷

关键词：

D O I：

10.1016/0008-6215(90)80137-R

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：

The isopropylidenation of erythritol, under conditions of kinetic control, employing 2-methoxypropene, yielded the 1,2:3,4- (1, 50%), the 1,4:2,3- (2, 18%), and the novel 1,3:2,4-diacetal (3, 5%). Under similar conditions, ribitol gave the known 1,2:4,5- (4, 36%) and 1,4:2,3-diacetal (7, 3%) together with the new 1,3:4,5- (8, 12%) and 1,3:2,5- diacetal (11, 5%), a further example of a dioxepane ring. 13C-N.m.r. and 1H-n.m.r. spectroscopy showed that the 1,3-dioxane rings in 3, 8, and 11 adopt chair conformations. In 9, the p-nitrobenzoate of 8, the dioxane chair is flattened. The product composition is compared with that from the equilibrated system. © 1990.

引用

页码：173 / 179

页数：7

共 29 条

[1] APPLICATION OF C-13 NMR IN A REEXAMINATION OF THE ISOPROPYLIDENATION OF D-RIBOSE DIETHYLDITHIOACETAL AND ERYTHRITOL [J].

ASLANISHOTORBANI, G ;

BUCHANAN, JG ;

EDGAR, AR ;

HENDERSON, D ;

SHAHIDI, P .

TETRAHEDRON LETTERS, 1980, 21 (18) :1791-1792

[2] C-NUCLEOSIDE STUDIES .16. THE ISOPROPYLIDENATION OF D-RIBOSE DIETHYL DITHIOACETAL AND RIBITOL - A NEW SYNTHESIS OF ALPHA-D-RIBOFURANUSYLETHYNE AND BETA-D-RIBOFURANOSYLETHYNE VIA 2,3-4,5-DI-O-ISOPROPYLIDENE-ALDEHYDO-D-RIBOSE [J].

ASLANISHOTORBANI, G ;

BUCHANAN, JG ;

EDGAR, AR ;

SHAHIDI, PK .

CARBOHYDRATE RESEARCH, 1985, 136 (FEB) :37-52

[3] ASSIGNMENT OF RING SIZE IN ISOPROPYLIDENE ACETALS BY C-13 NMR [J].

BUCHANAN, JG ;

CHACONFUERTES, ME ;

EDGAR, AR ;

MOORHOUSE, SJ ;

RAWSON, DI ;

WIGHTMAN, RH .

TETRAHEDRON LETTERS, 1980, 21 (18) :1793-1796

[4] ASSIGNMENT OF RING SIZE IN ISOPROPYLIDENE ACETALS BY C-13 NMR-SPECTROSCOPY [J].

BUCHANAN, JG ;

EDGAR, AR ;

RAWSON, DI ;

SHAHIDI, P ;

WIGHTMAN, RH .

CARBOHYDRATE RESEARCH, 1982, 100 (MAR) :75-86

[5] C-NUCLEOSIDE STUDIES .9. SYNTHESIS OF "3(5)-ALPHA-D-RIBOFURANOSYL-PYRAZOLE AND RELATED-COMPOUNDS [J].

BUCHANAN, JG ;

CHACONFUERTES, ME ;

STOBIE, A ;

WIGHTMAN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (11) :2561-2566

[6]

BUCK KW, 1964, CHEM IND-LONDON, P1623

[7] ASPECTS OF STEREOCHEMISTRY .11. ISOPROPYLIDENE DERIVATIVES OF L-ARABITOL AND RIBITOL [J].

BUKHARI, MA ;

WEBBER, JM ;

WESTWOOD, JH ;

LEHMANN, J ;

FOSTER, AB .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (APR) :2291-&

[8] ACETALATION STUDIES .2. ISOPROPYLIDENATION OF D-MANNITOL UNDER NEUTRAL CONDITIONS [J].

CHITTENDEN, GJF .

CARBOHYDRATE RESEARCH, 1980, 87 (02) :219-226

[9] CARBOHYDRATE CYCLIC ACETAL FORMATION AND MIGRATION [J].

CLODE, DM .

CHEMICAL REVIEWS, 1979, 79 (06) :491-513

[10] CHEMICAL-SHIFTS OF THE METHYL-GROUPS IN DI-O-ISO-PROPYLIDENE FURANOSES, AND THEIR RELATIONSHIP TO MOLECULAR-CONFORMATION AND SITE OF RING FUSION - SPIN-LATTICE RELAXATION MEASUREMENTS, AND MOTIONAL CHARACTERISTICS [J].

DAIS, P ;

PERLIN, AS .

CARBOHYDRATE RESEARCH, 1986, 146 (02) :177-191

← 1 2 3 →