Synthesis and Characterization of 5-Deoxy-3-O-methyl-5-C-[(R) - and (S)-phenylphosphinothioyl]-α- and β-d-xylopyranoses. The First Sugar Analogue Having a Phosphinothioyl Group in the Hemiacetal Ring
- 5 October 1987
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 16 (10) , 2081-2084
- https://doi.org/10.1246/cl.1987.2081
Abstract
Treatment of 5-deoxy-5-iodo-1,2-O-isopropylidene-β-O-methyl-α-d-xylofuranose with ethyl phenylphosphinothioate in the presence of sodium hydride, followed by the reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, and then with 0.5 M HCl–EtOH gave the title compounds, which were characterized as the 1,2,4-O-triacetates.This publication has 8 references indexed in Scilit:
- Pesticides and phosphorus.Journal of Synthetic Organic Chemistry, Japan, 1987
- Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranosesThe Journal of Organic Chemistry, 1985
- Synthesis of 1,2,3,5-tetra-O-acetyl-4-deoxy-4-C-[(RS)-ethylphosphinyl]-.alpha.,.beta.-D-ribo- and -L-lyxofuranoses and their structural analysis by 400-MHz proton nuclear magnetic resonanceThe Journal of Organic Chemistry, 1984
- Synthesis of 1,2,4-tri- O -acetyl-5-deoxy-5- C -[( R and S )-methoxy-phosphinyl]-3- O -methyl-α- and -β- d -xylopyranose, and their structural analysis by 400-MHz, proton nuclear magnetic resonance spectroscopyCarbohydrate Research, 1983
- Synthesis of 1,2,3,4,6-penta-O-acetyl-5-deoxy-5-C-[(RS)-ethylphosphinyl]-.alpha.- and .beta.-D-glucopyranoses and their structural analysis by 400-MHz proton nuclear magnetic resonanceThe Journal of Organic Chemistry, 1983
- Structural analysis of 5,6-dideoxy-5-C-[(R and S)-phenylphosphinyl]-L-ido-hexopyranoses by 400-MHz proton nuclear magnetic resonanceThe Journal of Organic Chemistry, 1982
- Branched-chain Sugars. III. Addition of Vinylmagnesium Bromide to 5,6-Dideoxy-1,2-O-isopropylidene-6-C-nitro-3-O-substituted-α-d-xylo-hex-5-enof uranosesBulletin of the Chemical Society of Japan, 1973
- Studies on the Organophosphorus InsecticidesAgricultural and Biological Chemistry, 1961