A novel seven-membered carbohydrate phostone

Tetrahedron Letters

Volumn 44, Issue 49, 2003, Pages 8797-8800

  Moravcova, Jitka ^a   Heissigerova, Helena ^a,b   Kocalka, Petr ^a   Imberty, Anne ^b   Sykora, David ^a   Fris, Miroslav ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b CNRS   (France)

Author keywords

Acetal group; Carbohydrates; Phosphonic acid; Phostone

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLUCOPYRANOSIDE; METHYL 2,3 DI O BENZYL 4,6 O BENZYLIDENE ALPHA(BETA) DEXTRO GLUCOPYRANOSIDE; REAGENT; TRIETHYL PHOSPHITE; TRIFLUOROMETHANESULFONIC ACID; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0242329815     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.187     Document Type: Article

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19. 3OH)) and its structure was confirmed by NMR measurements. Phostone 9a displays reactivity analogous to that of α-phostone 4 when subjected to the reagents described above. Thus, the course of this Michaelis-Arbuzov-type reaction does not depend on the anomeric configuration of the starting methyl 2,3-di-O-benzyl-4,6-O-benzylidene-D- glucopyranoside. In contrast to the D-gluco series, an attempt to prepare phostones derived from both methyl 2,3-di-O-benzyl-4,6-O-benzylidene-D- galactopyranosides was unsuccessful probably due to the steric hindrance of cis fused rings.