146512-86-9

Upstream product

• 100-44-7 benzyl chloride 
• 83541-13-3 (R)-(+)-6-(benzyloxy)-4-methylhexanal 
• 1117-61-9 (3R)-citronellol 
• 2385-77-5 (R)-Citronellal 
• 63175-00-8 (S)-3,7-dimethyl-6-oxooctanoic acid methyl ester 
• 84465-67-8 3R,7-Dimethyl-6S-hydroxy-octanoic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 146512-85-8 (3R)-1-benzyloxy-3-methyl-6-hexanol 
• 146512-84-7 (7R)-9-benzyloxy-3-oxa-4-oxo-2,7-dimethylnonane 
• 146512-83-6 (6R)-8-benzyloxy-3-oxo-2,6-dimethyloctane 
• 146512-81-4 methyl (3R)-3,7-dimethyl-6-oxooctanoate ethylene acetal 
• 146512-82-5 (6R)-8-hydroxy-3-oxo-3,7-dimethyloctanoic acid ethylene acetal 
• 146512-80-3 (3R,6S)-methyl 6-hydroxy-3,7-dimethyloctanoate 
• 68330-67-6 (4R,7S)-4-methyl-7-(1-methylethyl)oxepan-2-one 

Downstream Products

• 1446944-89-3 (3R,11R)-3,11-dimethylpentadecyl tosylate 
• 1446944-91-7 (3R,11S)-3,11-dimethylpentadecyl tosylate 
• 1446944-85-9 (3R,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne 
• 99427-19-7 (R)-3-Methylheptyl tosylate 
• 1070-32-2 (R)-(+)-3-Methyl-1-heptanol 
• 188692-81-1 (E)-(R)-9-Benzyloxy-7-methyl-non-2-en-1-ol 
• 188692-82-2 [(2R,3R)-3-((R)-6-Benzyloxy-4-methyl-hexyl)-oxiranyl]-methanol 
• 188692-80-0 (R)-9-Benzyloxy-7-methyl-non-2-yn-1-ol 
• 146512-87-0 (3R)-1-benzyloxy-3-methyloctane 

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.

Total synthesis of archaeal 36-membered macrocyclic diether lipid

Total synthesis of archaeal 36-membered macrocyclic diether lipid 2 is reported. The synthesis is based upon stereoselective preparation of functionalized isoprenoid chains, ether-linkage formation between the isoprenoid chains with a glycerol derivative,