Enantioselective syntheses of optically active or-amino acids from glycine t-butyl ester through Schiff base employing (+)-N-alkyl-10-camphorsulfonamides as chiral auxiliaries were described. Methylation of Schiff base 5 gave high asymmetric inductions, whereas ethylation, allylation and benzylation
Enzymatic synthesis of amino acid ester of butyl α-D-glucopyranoside
✍ Scribed by Jean Fabre; François Paul; Pierre Monsan; Casimir Blonski; Jacques Périé
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 202 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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The diastereoselective synthesis of α-amino esters from the glycine ester (I) employing the sulfonamides (II) as chiral auxiliaries works well for α-alkylation with methyl iodide. Ethylation, allylation, and benzylation proceeds with fair stereoselectivity, but pure diastereomers can be obtained by
Methyl 2-amino-2,6-dideoxy~-o-glucopyranoside-6-sulfonic acid (8) was prepared by oxidation of methyl 3,4-di-O-acety1-6-S-acetyl-2-benzamido-2-deo~-6-thio~-D-glu~p~anoside with hydrogen peroxide in acetic acid followed by N-and 0-deacylation with aqueous sodium hydroxide. Compound 8 was also obtaine