✦ LIBER ✦

Synthesis of 4-epi-2-deoxy-2-Heq-N-acetylneuraminic acid and 2,4-dideoxy-2-Heq N-acetylneuraminic acid

✍ Scribed by Babasaheb P. Bandgar; Erich Zbiral

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 549 KB
Volume: 270
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00013-j

No coin nor oath required. For personal study only.

✦ Synopsis

We have continued our work to develop novel analogues of sialic acid [1-4] that may specifically modulate the interaction between endogenous sialic acid and influenza virus haemagglutinin [3,5,6]. Functional groups of sialic acid that have been implicated for this virus-host recongnition are the glycerol side chain, N-acetyl group and the axially oriented carboxylic acid function [3]. In this report we describe the synthesis of two analogues, namely, 4-epi-2-deoxy-2-Heq-N-acetylneuraminic acid (4-epi-2-d-2-Heq-Neu5Ac) and 2,4-dideoxy-2-Heq-N-acetylneuraminic acid (2,4-d2-2-H~q-Neu5Ac).

📜 SIMILAR VOLUMES

Structural variations ofN-acetylneuramin

Structural variations ofN-acetylneuraminic acid, 23. Synthesis of 2-deoxy-2Heq-sialic Acid analogues structurally varied at C-4

✍ Hartmann, Michael ;Zbiral, Erich 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 772 KB

## Abstract 2‐Deoxy‐2‐H~eq~‐__N__‐acetylneuraminic acid (1a) has been shown to be a versatile mimic for sialosyl 2‐α‐glycosides to study the hemagglutinin‐sialic acid interaction. Starting with a 4‐oxo derivative of 2‐deoxy‐2‐H~eq~‐sialic acid, we obtained the 4‐__C__‐methyl~ax~ and 4‐__C__‐methyl~

Structural Variations ofN-Acetylneuramin

Structural Variations ofN-Acetylneuraminic Acid, 11, Synthesis of the 4-Methylumbelliferyl 2α-Glycosides of 7-Epi-, 8-Epi-, and 7,8-Bis(epi)-N-acetylneuraminic Acids, as well as of 7-Deoxy-, 8-Deoxy-, 9-Deoxy-, and 4,7-Dideoxy-N-acetylneuraminic Acids and Their Behaviour Towards Sialidase fromVibrio cholerae

✍ Zbiral, Erich ;Schreiner, Erwin ;Salunkhe, Mamikrao M. ;Schulz, Gerhard ;Kleinei 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 English ⚖ 942 KB

Stereoselective synthesis of 2-thioglyco

Stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid

✍ Alberto Marra; Pierre Sinaÿ 📂 Article 📅 1989 🏛 Elsevier Science 🌐 English ⚖ 628 KB

The synthesis of 2,3-didehydro-2,4-dideo

The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid: a potent influenza virus sialidase inhibitor

✍ Mark von Itzstein; Wen-Yang Wu; Betty Jin 📂 Article 📅 1994 🏛 Elsevier Science 🌐 English ⚖ 294 KB

The biochemistry and synthesis of sialidase inhibitors, in particular influenza virus sialidase inhibitors, has been of great interest to us [1][2][3]. The synthesis of a number of S-acetamido-2,6-anhydro-3,5-dideoxy-o-glycero-o-galacto-non-2-enonic acid (Neu5Ac2en, 1) analogues has received conside

Structural Variations ofN-Acetylneuramin

Structural Variations ofN-Acetylneuraminic Acid, 10. Synthesis of 2,7-, 2,8-, and 2,9-Dideoxy- and 2,4,7-Trideoxy-2,3-didehydro-N-acetylneuraminic Acids and Their Behavior Towards Sialidase fromVibrio cholerae

✍ Zbiral, Erich ;Schreiner, Erwin ;Christian, Rudolf ;Kleineidam, Reinhard G. ;Sch 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 English ⚖ 763 KB

Deoxy-nitrosugars 15th communication Syn

Deoxy-nitrosugars 15th communication Synthesis of N-acetylneuraminic acid and N-acetyl-4-epineuraminic Acid

✍ Franz Baumberger; Andrea Vasella 📂 Article 📅 1986 🏛 John Wiley and Sons 🌐 German ⚖ 800 KB

A synthesis of N-acetylneuraminic acid (1) and of N-acetyl-4-epineuraminic acid (2, R = H) from 2-acetamido-4,6-O-benzylidene-l,2-dideoxy-1 -nitro-D-mannopyranose (3) and 2-acetamido-l,2-dideoxy-4,6-0-isopropylidene-l -nitro-D-mannopyranose (4), respectively, is described. Michael addition of 3 and