STEREOSELECTIVE SYNTHESIS OF N-BOC-O-BENZYL-(4S,5S)-5-AMINO-4-HYDROXY-6-PHENYLHEXANOIC ACID, THE HYDROXYETHYLENE ISOSTERIC MOIETY OF POTENT HIV-1 PROTEASE INHIBITOR
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.
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| Published in | Tetrahedron letters Vol. 32; no. 16; pp. 1897 - 1898 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier
15.04.1991
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| Subjects | |
| Online Access | Get more information |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | CHAKRABORTY, TK GANGAKHEDKAR, KK |
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| References | TOMASSELLI, AG (WOS:A1990CH52900035) 1990; 29 DUREAULT, A (WOS:A1989AY26600028) 1989; 54 THAISRIVONGS, S (WOS:A1987H577300004) 1987; 30 BALDWIN, JE (WOS:A1989CE73200034) 1989 MCQUADE, TJ (WOS:A1990CK70500038) 1990; 247 MEEK, TD (WOS:A1990CG61400063) 1990; 343 SZELKE M (WOS:A1991FF55500015.6) 1983 STAMATATOS, L (WOS:A1984SX96100009) 1984; 40 |
| References_xml | – volume: 247 start-page: 454 year: 1990 ident: WOS:A1990CK70500038 article-title: A SYNTHETIC HIV-1 PROTEASE INHIBITOR WITH ANTIVIRAL ACTIVITY ARRESTS HIV-LIKE PARTICLE MATURATION publication-title: SCIENCE contributor: fullname: MCQUADE, TJ – volume: 29 start-page: 264 year: 1990 ident: WOS:A1990CH52900035 article-title: SUBSTRATE-ANALOG INHIBITION AND ACTIVE-SITE TITRATION OF PURIFIED RECOMBINANT HIV-1 PROTEASE publication-title: BIOCHEMISTRY contributor: fullname: TOMASSELLI, AG – start-page: 1852 year: 1989 ident: WOS:A1989CE73200034 article-title: THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: BALDWIN, JE – volume: 40 start-page: 1713 year: 1984 ident: WOS:A1984SX96100009 article-title: SYNTHESIS OF (4S,5R)-(+)-L-FACTOR, A PROPOSED AUTOREGULATOR OF ANTHRACYCLINE BIOSYNTHESIS publication-title: TETRAHEDRON contributor: fullname: STAMATATOS, L – volume: 30 start-page: 976 year: 1987 ident: WOS:A1987H577300004 article-title: RENIN INHIBITORS - DESIGN OF ANGIOTENSINOGEN TRANSITION-STATE ANALOGS CONTAINING NOVEL (2R,3R,4R,5S)-5-AMINO-3,4-DIHYDROXY-2-ISOPROPYL-7-METHYLOCTANOIC ACID publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: THAISRIVONGS, S – start-page: 579 year: 1983 ident: WOS:A1991FF55500015.6 publication-title: PEPTIDES STRUCTURE F contributor: fullname: SZELKE M – volume: 343 start-page: 90 year: 1990 ident: WOS:A1990CG61400063 article-title: INHIBITION OF HIV-1 PROTEASE IN INFECTED LYMPHOCYTES-T BY SYNTHETIC PEPTIDE ANALOGS publication-title: NATURE contributor: fullname: MEEK, TD – volume: 54 start-page: 5324 year: 1989 ident: WOS:A1989AY26600028 article-title: NUCLEOPHILIC OPENING OF CHIRAL BIS(AZIRIDINES) - A ROUTE TO ENANTIOMERICALLY PURE ALPHA-AMINO ALDEHYDES OR ACIDS AND POLYSUBSTITUTED PIPERIDINES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: DUREAULT, A |
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| Snippet | 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... |
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| StartPage | 1897 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | STEREOSELECTIVE SYNTHESIS OF N-BOC-O-BENZYL-(4S,5S)-5-AMINO-4-HYDROXY-6-PHENYLHEXANOIC ACID, THE HYDROXYETHYLENE ISOSTERIC MOIETY OF POTENT HIV-1 PROTEASE INHIBITOR |
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