C-STANNYLATED CARBOHYDRATE-DERIVATIVES .5. ENE-3-C-(ORGANOSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE AND ENE-3-C-(PHENYLSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE COMPOUNDS - X-RAY CRYSTAL AND MOLECULAR-STRUCTURE OF -3-C-(TRIPHENYLSTANNYLMETHYL)-ALPHA-D-ALLOFURANOSE

Authors
BURNETT LA DOIDGEHARRISON SMSV GARDEN SJ HOWIE RA TAYLOR OJ WARDELL JL
Citation
La. Burnett et al., C-STANNYLATED CARBOHYDRATE-DERIVATIVES .5. ENE-3-C-(ORGANOSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE AND ENE-3-C-(PHENYLSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE COMPOUNDS - X-RAY CRYSTAL AND MOLECULAR-STRUCTURE OF -3-C-(TRIPHENYLSTANNYLMETHYL)-ALPHA-D-ALLOFURANOSE, Journal of the Chemical Society. Perkin transactions. I, (14), 1993, pp. 1621-1628
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
14
Year of publication
1993
Pages
1621 - 1628
Database
ISI
SICI code
0300-922X(1993):14<1621:CC.E>2.0.ZU;2-7
Abstract
The crystal structure and the solid state (C-13 and Sn-119) and soluti on (H-1, C-13 and Sn-119) NMR spectra of ne-3-C-triphenylstannylmethyl -alpha-D-allofuranose (1; R = Ph) have been obtained. The structure of compound (1; R = Ph) is similar in both phases and contains a slightl y distorted tetrahedral tin atom (C-Sn-C valency angles range from 103 .8(3) to 114.9(5)-degrees!. The beta-oxygen atom at C(3) in compound ( 1; R = Ph) is 3.01 (1) A distant from Sn and is ideally sited to take part in nucleophilic assistance during Ph-Sn bond-cleavage reactions. Reactions of compound (1; R = Ph) and -di-0-isopropylidene-3-C-R3Sn-al pha-D-allofuranose with electrophiles (e.g., I2 or CF3CO2H) are also r eported.