70633-86-2

Upstream product

• 121980-49-2 (R)-4-Hydroxy-6-(2-phenyl-1-phenylselanyl-ethyl)-tetrahydro-pyran-2-one 
• 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 
• 158732-44-6 (R)-2-(2-hydroxy-4-phenyl-3-butenyl)-4-oxo-1,5-dioxaspiro<5.5>undec-2-ene 
• 158757-42-7 (R)-6-<(3E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl>-2,2-dimethyl-1,3-dioxin-4-one 
• 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 
• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 
• 96852-88-9 3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-hex-5-enofuranoside 
• 96852-87-8 1,2-O-isopropylidene-3-deoxy-5,6-di-O-methylsulphonyl-α-D-glucofuranose 
• 109536-54-1 methyl 1,2-O-isopropylidene-3,5-dideoxy-α-D-glucofuranose 
• 118117-15-0 ((3aR,5S,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetic acid 
• 58475-20-0 3,5-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranose 
• 1100-88-5 benzyltriphenylphosphonium chloride 

Downstream Products

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

Relevant academic research and scientific papers

Use of 1,3-dioxin-4-ones and related compounds in synthesis. XLIV. Asymmetric aldol reaction of 4-trimethylsiloxy-6-methylene-1,3-dioxines: Use of tartaric acid-derived (acyloxy)borane complex as the catalyst

A novel enantioselective synthesis of 1,3-dioxin-4-ones having a 2-hydroxylated alkyl group at the 6-position has been accomplished by chiral tartaric acid-derived acylborane-mediated aldol condensation of the silyl enol ether derived from 6-methyl-derivatives of 1,3-dioxin-4-one with achiral aldehydes.

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

An Alternative Approach to Mevinic Acid Analogues from Methyl (3R)-(-)-3-Hydroxyhex-5-enoate and an Extension to Unambiguous Syntheses of (6R)-(+)- and (6S)-(-)-Goniothalamin

Ozonolysis of the 3-silyloxyhexenoate 12, derived from the yeast reduction product methyl (3R)-(-)-3-hydroxyhex-5-enoate 6 and having an enantiomeric enrichment of 78percent, followed by Wittig homologation and selenolactonization leads to the unsaturated mevinic acid analogues 17 and 18.Subsequent dehydration gives both enantiomers of the natural product goniothalamin 20 and 21.

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).