119005-71-9Relevant academic research and scientific papers
Regioselective synthesis of naphthoquinone/naphthoquinol-carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity
Chakraborty, Soumen,Das, Gaurav,Ghosh, Surajit,Mal, Dipakranjan
, p. 10636 - 10647 (2016/11/30)
An efficient and regioselective synthetic route to naphthoquinone/naphthoquinol-carbohydrate hybrids has been developed. It is based upon anionic annulation of 3-nucleofugalphthalides with an acrylate appended sugar moiety. In each of the annulations studied, the arene-carbohydrate hybrids were obtained in good to excellent yields. The in vitro cytotoxic activity of the synthetic naphthoquinone/naphthonol-carbohydrate hybrids were evaluated against the human cervical cancer cell line (HeLa), and a few of them were found to exhibit potent anticancer activity against the cell line.
An in-depth study on ring-closing metathesis of carbohydrate-derived α-alkoxyacrylates: Efficient syntheses of DAH, KDO, and 2-deoxy-β-KDO
Hekking, Koen F. W.,Moelands, Marcel A. H.,Van Delft, Floris L.,Rutjes, Floris P. J. T.
, p. 6444 - 6450 (2007/10/03)
Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-β-KDO are described. Ring-closing metathesis (RCM) of highly functionalized α-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further
Synthesis of 2-deoxy-α- and -β-D-arabino-hexopyranosyl phosphonic acids and related compounds; analogues of early intermediates in the shikimate pathway
Barnes, Nigel J.,Probert, Mark A.,Wightman, Richard H.
, p. 431 - 438 (2007/10/03)
Treatment of 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranose 18 with trimethyl phosphite in the presence of trimethylsilyl triflate gave a separable mixture of dimethyl (3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosyl)phosphonate 19 (35%) and the β-anomer 20 (60%). The diethyl analogue of compound 20 could be prepared stereoselectively from tributyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranosyl)stannane 21 and diethyl chlorophosphate. Reaction of 1,3,4,6-tetra-O-acetyl-2-deoxy-D-arabino-hexopyranose 23 with trimethyl phosphite and trimethylsilyl triflate gave dimethyl (3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranosyl)phosphonate 25 and the β-anomer 27 with some α-selectivity. Deprotection of compounds 25 and 27 gave the phosphonic acids 11 and 12 respectively. The esters 25 and 27 could be converted into methyl 3,4,6-tri-O-acetyl-2-deoxy-1-(dimethoxyphosphoryl)-β-D-arabino- hexopyranoside 31 by free-radical bromination followed by methanolysis, and diethyl [3,4,6-tri-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranosyl) phosphonate 33 was prepared by interaction of the 1-lithioglucal with diethyl chlorophosphate. Metallation of stannane 21 and reaction with methyl chloroformate gave methyl 2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-gluco-heptonate 35 which could be alkylated with tert-butyl bromoacetate to give, after deprotection, 3,7-anhydro-3-carboxy-2,4-dideoxy-D-gluco-octonic acid 14.
Diastereoselective Free-radical Reactions. Part 1. Preparation of 2-Deoxy-β-glycosides by Synthesis and Reductive Decarboxylation of 3-Deoxyulosonic Acid Glycosides
Crich, David,Ritchie, Timothy J.
, p. 945 - 954 (2007/10/02)
A general procedure for the synthesis of 2-deoxy-β-D-glycosides involving the preparation of 3-deoxyulosonic acid glycosides from glycals and their reductive decarboxylation is described.
