Syntheses of 2-O-glycosyl derivatives of N-acetyl-d-neuraminic acid
โ Scribed by Haruo Ogura; Kimio Furuhata; Masayoshi Itoh; Yoshiyasu Shitori
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- English
- Weight
- 872 KB
- Volume
- 158
- Category
- Article
- ISSN
- 0008-6215
No coin nor oath required. For personal study only.
๐ SIMILAR VOLUMES
N-Acetylneuraminic acid (1) can be transformed into the methyl a-u-ketoside 2 which, by reaction with methanesulfonyl chloride, yields the corresponding 4-0 mesylate 3 and the 4.7-di-0 -mesylate 4 as a by-product. Compound 3 reacts with Nal giving the 4-dcoxy-4-iodo compound 5 with cquatorial orient
Aldol condensation of la with potassium di-tert-butyloxaloacetate yields the two epimeric 6-thiosialic acids 2 and 3. As opposed to this, reaction between thiofuranose 6 \_ and nickel (II)/oxaloacetate affords 6-thio-N-acetyl-D-neuraminic acid \_Ic. Substituting sulfur for oxygen in the pyranosering