83541-13-3

Upstream product

• 96154-40-4 3,7-dimethyl-6-octenyl benzyl ether 
• 1117-61-9 (3R)-citronellol 
• 100-44-7 benzyl chloride 
• 2385-77-5 (R)-Citronellal 
• 100-39-0 benzyl bromide 
• 83541-12-2 (R)-(+)-citronellyl benzyl ether 

Downstream Products

• 86527-49-3 [(Z)-(R)-7-(1-Ethoxy-ethoxy)-3-methyl-non-6-en-8-ynyloxymethyl]-benzene 
• 1065253-22-6 (5R)-7-(benzyloxy)-1-(3-methoxy-5-methylphenyl)-5-methylheptan-2-ol 
• 1345135-01-4 (2R,6E,10R)-tert-butyldimethylsilyl 12-benzyloxy-2,6,10-trimethyl-6-dodecenyl ether 
• 1345135-03-6 (2R,6S,7S,10R)-12-benzyloxy-1-tert-butyldimethylsilyloxy-2,6,10-trimethyldodecane-6,7-diol 
• 1345135-05-8 (2R,6S,7R,10R)-12-benzyloxy-1-tert-butyldimethylsilyloxy-6,7-epoxy-2,6,10-trimethyldodecane 
• 1345135-07-0 (2R,6R,10R)-12-benzyloxy-1-tert-butyldimethylsilyloxy-2,6,10-trimethyldodecan-6-ol 
• 1345135-09-2 (2R,6R,10R)-1-tert-butyldimethylsilyloxy-12-phenylsulfonyl-2,6,10-trimethyldodecan-6-ol 
• 1345135-31-0 (2R,6R,10R,14E)-1,16-bis-(tert-butyldimethylsilyloxy)-12-phenylsulfonyl-2,6,10,14-tetramethyl-14-hexadecen-6-ol 
• 1345134-98-6 (2E,6R)-2,6-dimethyl-8-benzyloxy-2-octen-1-ol 
• 1345135-38-7 (7R,11R,15R)-16-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-11-hydroxy-5-phenylsulfonyl-3,7,11,15-tetramethyl-4-hexadecanone 
• 1345135-16-1 (7R,11R,15R)-16-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-11-hydroxy-3,7,11,15-tetramethyl-4-hexadecanone 

Relevant academic research and scientific papers

Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol

Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.

Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal

The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2- octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three wellestablished procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.

Stereoselective synthesis of (-)-PF1163A via prins cyclization

A highly stereoselective and convergent total synthesis of PF1163 A is described while proving the versatility of Prins cyclization in natural product synthesis. The Prins cyclization, Yamaguchi esterification, and ring-closing metathesis reactions are th