FACILE STEREOSELECTIVE SYNTHESES OF 4 OF THE 6 1,2,3,4-CYCLOHEXANETETROLS - INCREASING THE ACCESSIBILITY OF CYCLITOLS FOR PROBING THE MOLECULAR RECOGNITION OF SACCHARIDES

Authors
HUANG CY CABELL LA ANSLYN EV
Citation
Cy. Huang et al., FACILE STEREOSELECTIVE SYNTHESES OF 4 OF THE 6 1,2,3,4-CYCLOHEXANETETROLS - INCREASING THE ACCESSIBILITY OF CYCLITOLS FOR PROBING THE MOLECULAR RECOGNITION OF SACCHARIDES, Synthetic communications, 24(19), 1994, pp. 2757-2764
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
24
Issue
19
Year of publication
1994
Pages
2757 - 2764
Database
ISI
SICI code
0039-7911(1994)24:19<2757:FSSO4O>2.0.ZU;2-9
Abstract
New and stereoselective syntheses of (1,2,3/4)-, (1,2/3,4)-, (1,4/2,3) -, and (1,2,4/3)-cyclohexanetetrols (1, 2, 3, and 4 respectively) are described. The known syn and anti 1,4-cyclohex-2-enediols 9 and 10 wer e used as starting materials. Diols 9 and 10 were allow to react with OsO4 to directly form 3 and 1 respectively. Diols 9 and 1 0 were epoxi dized with MCPBA, which yielded 4 and 2 after acid catalyzed epoxide o pening.