Syntheses of the enantiomers of 1-deoxynojirimycin and 1- deoxyaltronojirimycin via chemo- and diastereoselective olefinic oxidation of unsaturated amines

Journal of Organic Chemistry

Volumn 75, Issue 23, 2010, Pages 8133-8146

  Bagal, Sharan K ^b   Davies, Stephen G ^a   Lee, James A ^a   Roberts, Paul M ^a   Scott, Philip M ^a   Thomson, James E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL HPLC; CHLOROMETHYL; DEOXYNOJIRIMYCIN; DEPROTECTION; DIASTEREOISOMERS; DIASTEREOSELECTIVE; EPOXIDE RING OPENING; FUNCTIONALIZED; GROUP MANIPULATIONS; REGIO-SELECTIVE; RING CONTRACTION; UNSATURATED AMINES;

CHIRALITY; FUNCTIONAL GROUPS; OXIDATION;

ENANTIOMERS;

1 DEOXYALTRONOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN DERIVATIVE; 3 CHLOROPERBENZOIC ACID; AMINE; AZEPINE DERIVATIVE; BENZYL ALCOHOL; BORIC ACID; EPOXIDE; FLUOROBORIC ACID; FUNCTIONAL GROUP; N ( 1 ) 1' ( 1'' NAPHTHYL)ETHYL 2,7 DIHYDRO 1H AZEPINE; N ( 1 ) 1' ( 1'' NAPHTHYL)ETHYL 3 HYDROXY 4 BENZYLOXY 5,6 EPOXYAZEPANE; N 1 BENZYL 2 CHLOROMETHYL 3 BENZYLOXY 4,5 EPOXYPIPERIDINE; N 1 BENZYL 3 HYDROXY 4 BENZYLOXY 2,3,4,7 TETRAHYDRO 1H AZEPINE; N 1 BENZYL 3 HYDROXY 4 BENZYLOXY 5,6 EPOXYAZEPANE; NITROGEN; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; ATOM; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DEPROTECTION REACTION; DIASTEREOISOMER; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OLEFINATION; OLEFINIC OXIDATION; OXIDATION; RING OPENING; STEREOCHEMISTRY;

1-DEOXYNOJIRIMYCIN; ALKENES; AMINES; EPOXY COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 78650285219     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101756g     Document Type: Article

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