## A stereoselective synthesis of rhe hydroxyerhylene dipeptide isostere. ~2.~,4S.SP~-_~-(rmina-6 cyclQ~Kyl~4-hydrQxy-2-isQpropyl hawzoic acid n-bury1 amidffrom Bat-L-phenyinlmurw is described.
The synthesis of (2S,4S,5S) -5-(N-BOC)-amino-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid lactone, an hydroxyethylene dipeptide isostere precusor
โ Scribed by Prasun K. Chakravarty; Stephen E. de Laszlo; Carol S. Sarnella; James P. Sprinnger; Paul F. Schuda
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 212 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A synthetic approach to the butyrolactones of (2SR,4SR)-S(S)-(N-Bo)-amino-6-cyclohexyl-4-hy~oxy-2-i~propyl hexanoic acid from
๐ SIMILAR VOLUMES
N-Boc-O-benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid is synthesized in a highly stereoselective way involving, as a key step, regioselective opening of carbohydrate-based aziridine ring.
Two stereoisomers of the title compound have been synthesized from the methyl ester of N-Boc L-valine. The aminoester was initially converted into an a%-amino a,b-unsaturated ketone via a phosphonoketone and a Horner-Emmons olefination with acetaldehyde. Hydrocyanation of the enone with diethylalumi
The N-Boc dihydroxyethylene dipeptide isostere 7 and its N-Boc 3-(thiazol-4-ylJalany1 derivative 8 were synthesized, without purification of intermediates, from (4S~R)-22-dimethyl-4-(2-methy~propylJ-5-hydro~~thyl-l.3-dioxolane (361, in 24 and 32% overall yield, respectively, Alcohol 38 was readily p