A NEW APPROACH TO THE STEREOSPECIFIC SYNTHESIS OF A DIHYDROXYETHYLENE ISOSTERE

A dihydroxyethylene isostere, (2S,3R,4S)-4-amino-5-cyclohexyl-1-morpholino-2,3-pentanediol, which is a component of non-peptidic, orally active, low-molecular-weight renin inhibitors, was synthesized sterospecifically starting from prochiral divinylcarbinol via the Sharpless epoxidation.

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 38; no. 12; pp. 3460 - 3462
Main Authors ATSUUMI, S, NAKANO, M, KOIKE, Y, TANAKA, S, FUNABASHI, H, HASHIMOTO, J, MORISHIMA, H
Format Journal Article
LanguageEnglish
Published TOKYO Pharmaceutical Soc Japan 1990
Maruzen
Subjects
Aliphatic compounds
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Exact sciences and technology
Life Sciences & Biomedicine
Organic chemistry
Pharmacology & Pharmacy
Physical Sciences
Preparations and properties
Science & Technology
DESIGN
DIHYDROXYETHYLENE ISOSTERE
(2S,3R,4S)-4-AMINO-5-CYCLOHEXYL-1-MORPHOLINO-2,3-PENTANEDIOL
ANALOGS
SHARPLESS EPOXIDATION
DIVINYLCARBINOL
STEREOSPECIFIC SYNTHESIS
EPOXIDATION
POTENT
PEPTIDES
INVIVO
BIOLOGICAL-ACTIVITY
FK-506
RENIN INHIBITOR
SELECTIVITY
RENIN INHIBITORS
Diol
Renin
Sharpless epoxidation
Absolute configuration
Oral administration
Epoxidation
Enzyme inhibitor
Stereospecificity
Primary amine
Biological activity
Organic compounds
Oxygen nitrogen heterocycle
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Summary:A dihydroxyethylene isostere, (2S,3R,4S)-4-amino-5-cyclohexyl-1-morpholino-2,3-pentanediol, which is a component of non-peptidic, orally active, low-molecular-weight renin inhibitors, was synthesized sterospecifically starting from prochiral divinylcarbinol via the Sharpless epoxidation.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.38.3460