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Simple syntheses of 3,4-dideoxy-oct-2-ulosonic acids

โœ Scribed by Tony K.M. Shing

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
137 KB
Volume
33
Category
Article
ISSN
0040-4039

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๐Ÿ“œ SIMILAR VOLUMES

Enantiospecific syntheses of 3,4-dideoxy
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โœ Tony K.M. Shing ๐Ÿ“‚ Article ๐Ÿ“… 1992 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 805 KB

Ethyl 5,6,7,8-tetra-Oacetyl-3,4-dideoxy-D-arabiflPoct-2-ulosonate and ethyl 3,4dideoxy-5.6:7,8-di-Oisopropylidene-D-afaM?o-oct-2-ulosonate have been synthesised from peracetylated and bisacetonated Mehydo-Darabinose respectively by a two stage procedure: Wittig reaction and catalytic hydrogenation.

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Reactions of l-ethoxyvinyllithium with isopropylidene or benzyl protected sugar lactones afforded the corresponding hemiacetals which, on ozonolysis, gave the ethyl 2-ulosonates. This allowed a rapid and efficient synthesis of 3-deoxy-D-manno-oct-2-ulosonic acid (KDO).

New Route to 3-Deoxy-2-Ulosonic Acids; T
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Syntheses of KDO and KDN by alkylation of 2-alkoxy-2-cyanoacetate anion, an acyl anion equivalent of alkyl glyoxylate, with a sugar-derived iodide and triflate are described.@ 1997 Elsevier Science Ltd. 3-Deoxy-D-manno-2-octulosonic acid (KDO; 1)1)and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid