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

页码：1027 / 1035

页数：9

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
BREHM, M
DAUBEN, WG
KOHLER, P
LICHTENTHALER, FW
[J]. 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
DEFFIEUX, G
BAUTE, R
BAUTE, MA
ATFANI, M
CARPY, A
[J]. PHYTOCHEMISTRY, 1987, 26 (05) : 1391 - 1393
[5] STEREOSPECIFIC SYNTHESIS OF (S,S)-PALYTHAZINE FROM D-GLUCOSE
JARGLIS, P
LICHTENTHALER, FW
[J]. 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
LICHTENTHALER, FW
ELASHRY, ESH
GOCKEL, VH
[J]. 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
NAKAMURA, T
NAITO, A
TAKAHASHI, Y
AKANUMA, H
[J]. 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
Suzuki, M
Kametani, S
Uchida, K
Akanuma, H
[J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1996, 240 (01): : 23 - 29

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