First synthesis of the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 19,p. 1993-1994
- https://doi.org/10.1039/c39950001993
Abstract
Recation of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iododemercuriation stereoselectivity affords the α-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group, treatment of the iodide with triethylphosphite to afford the corresponding phosphonate, deprotection of the hydroxy group, oxidation, oximation, catalytic hydrogenation and acetylation, afford the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate.Keywords
This publication has 19 references indexed in Scilit:
- Enzymes in Organic Synthesis: Application to the Problems of Carbohydrate Recognition (Part 2)Angewandte Chemie International Edition in English, 1995
- Glycal‐1‐ylmethylphosphonates – precursors of glycosyltransferase inhibitorsEuropean Journal of Organic Chemistry, 1994
- Stereoselective synthesis of the isosteric bisphosphono analogue of β-D-fructose 2,6-bisphosphateJournal of the Chemical Society, Chemical Communications, 1990
- Synthesis of C-arabinofuranosyl compounds. Phosphonate and carboxylate isosteres of d-arabinose 1,5-bisphosphateCarbohydrate Research, 1987
- Deoxy‐nitrosugars 12th communication Synthesis of isosteric mono‐phosphonate analogues of β‐and α‐D‐fructose 2,6‐bisphosphateHelvetica Chimica Acta, 1986
- Synthesis of the phosphono analogues of α- and β-d-mannopyranosyl phosphateCarbohydrate Research, 1984
- 2,5-Anhydro-1-deoxy-1-phosphono-D-altritol, an isosteric analog of .alpha.-D-ribofuranose 1-phosphateJournal of Medicinal Chemistry, 1984
- A facile route to methylenephosphonate sugars substituted at the anomeric carbonTetrahedron Letters, 1983
- Stereospecific synthesis of ethyl (2-acetamido-2-deoxy-α-d-glucopyranosyl)-acetateCarbohydrate Research, 1983
- Stereospecific synthesis of the phosphono analogs of .alpha.- and .beta.-D-glucose 1-phosphateThe Journal of Organic Chemistry, 1982