4360-86-5

Upstream product

• 64770-20-3 2-hexyl-2-methylmalonic acid diethyl ester 
• 544-10-5 1-Chlorohexane 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 3004-93-1 2-methyloctanoic acid 
• 1610613-88-1 1-O-benzyl-3-O-(heptadec-16-en-1-yl)-2-O-[(10RS)-10-methylhexadecyl]-sn-glycerol 
• 1610613-90-5 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol 
• 1610613-93-8 3,3′-O,O-(dotriacontane-1,32-diyl)bis{2-O-[(10RS)-10-methylhexadecyl]-sn-glycerol} 
• 49642-49-1 2-methyl-1-octanal 
• 117555-29-0 Toluene-4-sulfonic acid 2-methyl-octyl ester 
• 17001-26-2 (10RS)-10-methylhexadecanoic acid 
• 818-81-5 2-methyloctan-1-ol 

Relevant academic research and scientific papers

Structure-property relationships in a series of diglycerol tetraether model lipids and their lyotropic assemblies: The effect of branching topology and chirality

Three novel diglycerol tetraether lipids with one membrane-spanning chain have been synthesized. These lipids contain only two or four racemic methyl branches at selected positions of the hydrophobic chains in contrast to natural lipids from archaebacterial membranes with an isoprenoid substitution pattern. The insertion of the methyl moieties was realized starting from either (RS)-citronellyl bromide or the inexpensive methyl malonic acid ethyl ester. For chain elongation the Cu-catalysed Grignard coupling reaction was used. The preparation of diglycerol tetraethers was either performed by condensing suitable blocked monoglycerol diethers by Grubbs metathesis or by reaction of the transmembrane C32-chain with blocked glycerols followed by further alkylation steps. Finally, we could show that the resulting lipids can form closed lipid vesicles comparable to the optically pure counterparts. Therefore, these much simpler lipids compared to the natural lipids from archaebacterial membranes are also suitable for preparation of stable tailored liposomes. This journal is the Partner Organisations 2014.

2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa: Alcohol chain length and enantioselectivity

Enantiomerically pure (R)-2-methyldecanoic acid and (S)-2-methyl-1-decanol were prepared in a multi gram scale by esterification reactions catalysed by lipase from Candida rugosa. The enantiomeric ratios (E-values) were determined as a function of the chain length of the alcohol used as the complementary substrate in cyclohexane. In the resolution of 2-methyldecanoic acid the highest value (E = 37 ± 5) was obtained, when either 2-hexanol, 1-heptanol or 1-octanol were used. In contrast, when resolving 2-methyloctanoic acid, the E-values increased continually with increasing chain length of the alcohol used. 1-Hexadecanol gave the highest value: E > 100. The E-values were determined from the enantiomeric excess (ee) of the product at a conversion below 0.4. After two consecutive esterification reactions enantiomerically pure (R)-2-methyldecanoic acid, >99.8% ee, and after subsequent reduction of the ester produced, (S)-2-methyl-1-decanol, 96.7% ee, were obtained.