70670-14-3

Basic information

• Product Name: (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one
• Synonyms: (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one
• CAS NO: 70670-14-3
• Molecular Weight: 218.252
• Mol File: 70670-14-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one(70670-14-3)
• EPA Substance Registry System: (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one(70670-14-3)

Safety Data

• Hazardous Substances Data: 70670-14-3(Hazardous Substances Data)

Upstream product

• 1100-88-5 benzyltriphenylphosphonium chloride 
• 118117-17-2 methyl 3,5-dideoxy-β-D-glucofuranuronate 
• 103338-09-6 methyl (E,3S^*,5R^*)-3,5-dihydroxy-7-phenyl-6-heptenoate 
• 109583-02-0 methyl (3S,5R,6E)-7-phenyl-3,5-isopropylidenedioxy-6-heptenoate 
• 136030-21-2 (E)-(3S,5R)-3,5-Dihydroxy-7-phenyl-hept-6-enoic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 158732-39-9 (5R)-6-(2-hydroxy-4-phenyl-3-butenyl)-2,2-dimethyl-[1,3]-dioxin-4-one 
• 158732-47-9 methyl (R,E)-5-(tert-butyldimethylsilyloxy)-3-oxo-7-phenylhept-6-enoate 
• 158732-50-4 4-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-phenyl-but-3-enyl]-1,5-dioxa-spiro[5.5]undec-3-en-2-one 
• 141928-29-2 Methyl (+/-)-(6E)-5-Hydroxy-3-oxo-7-phenyl-6-heptenoate 
• 58475-20-0 3,5-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranose 
• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 
• 118117-15-0 ((3aR,5S,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetic acid 
• 109536-54-1 methyl 1,2-O-isopropylidene-3,5-dideoxy-α-D-glucofuranose 

Downstream Products

• 22639-28-7 (R)-goniothalamin 
• 118117-14-9 (4S,6R)-3,4,5,6-tetrahydro-6-(2-phenylethenyl)-4-dimethyl-t-butylsilyloxy-2H-pyran-2-one 
• 118117-14-9 (R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-styryl)-tetrahydro-pyran-2-one 
• 118117-14-9 (4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-styryl)-tetrahydro-pyran-2-one 
• 118204-01-6 (6R)-6-<(Z)-styryl>-5,6-dihydro-2H-pyran-2-one 

Relevant articles and documents

Stereoselective reduction of β,δ-diketo esters. A novel strategy for the synthesis of artificial HMG-CoA reductase inhibitors

Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe-NaBH4 in tetrahydrofuran-methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe-NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.

Enzyme-catalyzed Lactonization of Methyl (+/-)-(E)-3,5-Dihydroxy-7-phenyl-6-heptenoates. - A Comparison of the Behaviour of syn- and anti-Compounds

3-Hydroxy lactones with a high enantiomeric excess were obtained by the lipase-catalyzed enantioselective lactonization of racemic syn- and anti-3,5-dihydroxy carboxylic esters.The (5S)-lactones were formed predominantly from both diols with pancreatin as

SYNTHESIS OF THE 5,6-DIHYDRO-2-PYRONE MOIETY OF (+)-ANAMARIN

The α,β-unsaturated δ-lactone (+)-goniothalamin (18E) and its Z-isomer (18Z), which contain the lactonic moiety of (+)-anamarin (1), have been synthesized from the known 1,2-O-isopropylidene 3-deoxy-α-D-glucofuranose (7).In the key step, methyl 3,5-dideoxy-β-D-glucofuranuronate (15) was treated with benzylidenetriphenylphosphorane in dimethyl sulphoxide to give the E- and Z-β-hydroxy δ-lactones (17).These were then transformed into the 5,6-dihydro-2-pyrones (18), and also into the aldehyde (20), intended for use in a total synthesis of (+)-anamarin (1).