Structure of 1,5-anhydro-D-fructose: X-ray analysis of crystalline acetylated dimeric forms

被引：24
作者：
Andersen, SM
Lundt, I
Marcussen, J
Sotofte, I
Yu, SK
机构：
[1] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark
[2] Danisco AS, Danisco Biotechnol, DK-1001 Copenhagen K, Denmark
[3] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
来源：
JOURNAL OF CARBOHYDRATE CHEMISTRY | 1998年 / 17卷 / 07期
关键词：
D O I：
10.1080/07328309808001881
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：
Acetylation of 1,5-anhydro-D-fructose under acidic conditions gave two crystalline acetylated dimeric forms, which by X-ray analysis were shown to be diastereomeric spiroketals formed between C-2 and C-2/C-3. The structures of the compounds differed only at the configuration at C-2. Acetylation or benzoylation of 1,5-anhydro-D-fructose in pyridine yielded 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enos-2-ulopyra-nose or crystalline 1,5-anhydro-3,6-di-O-benzoyl-4-deoxy-D-glycero-hex-3-enos-2-ulo-pyranose.
引用
收藏
页码：1027 / 1035
页数：9
相关论文
共 17 条
[1]  
[Anonymous], ANGEW CHEM
[2]   ENANTIOMERICALLY PURE BUILDING-BLOCKS FROM SUGARS .5. PROOF OF THE (S,S) CONFIGURATION OF (-)-BISSETONE BY SYNTHESIS FROM D-GLUCOSE [J].
BREHM, M ;
DAUBEN, WG ;
KOHLER, P ;
LICHTENTHALER, FW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (12) :1271-1273
[3]  
BREHM M, 1987, ANGEW CHEM, V99, P1318
[4]   1,5-D-ANHYDROFRUCTOSE, THE PRECURSOR OF THE PYRONE MICROTHECIN IN MORCHELLA-VULGARIS [J].
DEFFIEUX, G ;
BAUTE, R ;
BAUTE, MA ;
ATFANI, M ;
CARPY, A .
PHYTOCHEMISTRY, 1987, 26 (05) :1391-1393
[5]   STEREOSPECIFIC SYNTHESIS OF (S,S)-PALYTHAZINE FROM D-GLUCOSE [J].
JARGLIS, P ;
LICHTENTHALER, FW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (02) :141-142
[6]  
Kametani S, 1996, J BIOCHEM-TOKYO, V119, P180
[7]   A CONVENIENT ACCESS TO 1,5-ANHYDROKETOSES [J].
LICHTENTHALER, FW ;
ELASHRY, ESH ;
GOCKEL, VH .
TETRAHEDRON LETTERS, 1980, 21 (15) :1429-1432
[8]   OXIDATION OF 1,5-ANHYDRO-D-GLUCITOL TO 1,5-ANHYDRO-D-FRUCTOSE CATALYZED BY AN ENZYME FROM BACTERIAL-MEMBRANES [J].
NAKAMURA, T ;
NAITO, A ;
TAKAHASHI, Y ;
AKANUMA, H .
JOURNAL OF BIOCHEMISTRY, 1986, 99 (03) :607-613
[9]  
NAKAMURA T, 1988, CHEM ABSTR 110835, V109
[10]   Production of 1,5-anhydroglucitol from 1,5-anhydrofructose in erythroleukemia cells [J].
Suzuki, M ;
Kametani, S ;
Uchida, K ;
Akanuma, H .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1996, 240 (01) :23-29
12