𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A Practical Synthesis of the Dihydroxyethylene Dipeptide Isostere, (2S, 3R, 4S) 2-[(tert-Butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane, from D-Isoascorbic Acid

✍ Scribed by William R. Baker; Stephen L. Condon

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
249 KB
Volume
33
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

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 preparedfrom inexpensive and commerically available D-isoascorbic acid in four steps. The synthesisfeautred a stereoselective addition of cycloheqlmethyRithium to the dimethyl hydrazone of (4S...U)-2,2-dimethyl4-(2methylpropyl)-S-formyl-1 $-dioxolane (4).

πŸ“œ SIMILAR VOLUMES

Synthesis of the Nonpeptide Renin Inhibi
Synthesis of the Nonpeptide Renin Inhibitor A-68064 and the ACE Inhibitor Methyl Enalaprilat from (5S)-2,3,5,6-Tetrahydro-5-alkyl-N-(tert-butyloxycarbonyl-4H-1,4-oxazine-2-ones
✍ William R. Baker; Stephen L. Condon πŸ“‚ Article πŸ“… 1992 πŸ› Elsevier Science 🌐 French βš– 218 KB

## The nonpeptide renin inhibitor, A-68064, and the ACE inhibitor methyl enalaprilat were synthesizedfrom (5S) 235,6-tetrahydro-S-benryI(bury2)-N-(tert-buto~car~nyl)~H~l fl-oxazine-2-ones la and 76, and (5s) 2.3,S,6-tetrahydro-5methyl-N-(fert-butoxycarbonyl)-4H-l.4-oxazine-2-one 12, respectively.