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Stereoselective acetylation of racemic 7-[N,N′-bis-(benzyloxycarbonyl)-N-(guanidinoheptanoyl)]-α-hydroxyglycine
- Source :
- Tetrahedron: Asymmetry. 8:1767-1771
- Publication Year :
- 1997
- Publisher :
- Elsevier BV, 1997.
-
Abstract
- Chiral intermediate (−)-7-[ N , N ′-Bis(benzyloxycarbonyl)- N -(guanidinoheptanoyl)]-α-acetoxyglycine 2 was prepared for the total synthesis of a (−)-15 deoxyspergualin, an antitumor antibiotic and immunosuppressive agent. The stereoselective acetylation of racemic 7-[ N , N ′-Bis(benzyloxycarbonyl)- N -(guanidinoheptanoyl)]-α-hydroxyglycine 1 was carried out in methyl ethyl ketone (MEK) using lipase from Pseudomonas sp. (lipase AK). Vinyl acetate was used as an acylating agent. A reaction yield of 48% (theoretical max 50%) and an optical purity of 98% were obtained for S-(−)-acetate 2 . The unreacted alcohol (+)- 1 was obtained in 41% yield and 98.5% optical purity.
- Subjects :
- chemistry.chemical_classification
Ketone
biology
Chemistry
Stereochemistry
Organic Chemistry
Total synthesis
Catalysis
Inorganic Chemistry
Acylation
chemistry.chemical_compound
Yield (chemistry)
Vinyl acetate
biology.protein
Stereoselectivity
Physical and Theoretical Chemistry
Lipase
Enantiomeric excess
Subjects
Details
- ISSN :
- 09574166
- Volume :
- 8
- Database :
- OpenAIRE
- Journal :
- Tetrahedron: Asymmetry
- Accession number :
- edsair.doi...........d6b885e40c44fcfa3b483ab3863b89ef