70774-95-7

Upstream product

• 629-80-1 n-hexadecylaldehyde 
• 108-18-9 diisopropylamine 
• 57-10-3 1-hexadecylcarboxylic acid 
• 119119-52-7 Tetradecylmalonsaeureethyltrimethylsilylester 
• 119119-53-8 α-Tetradecyl-β-keto-stearinsaeureethylester 
• 119119-51-6 Tetradecylmalonsaeuremonoethylester 
• 119119-54-9 α-Tetradecyl-β-hydroxy-stearinsaeureethylester 
• 17369-87-8 methyl corynomycolate 
• 60715-65-3 methyl α-palmitoyl palmitate 
• 112-39-0 hexadecanoic acid methyl ester 
• 102496-50-4 (R)-2-Hydroxy-6-((R)-1-hydroxy-hexadecyl)-3-undecyl-cyclohex-2-enone 
• 17369-87-8 methyl (2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoate 
• 87333-63-9 methyl (2RS,3SR)-3-hydroxy-2-tetradecyloctadecanoate 

Downstream Products

• 62054-35-7 6-O-<(2RS,3SR)-3-hydroxy-2-tetradecyloctadecanoyl>-α,α-trehalose 
• 17369-87-8 methyl (2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoate 

Relevant academic research and scientific papers

Adjuvant properties of a simplified C32 monomycolyl glycerol analogue

A simplified C32 monomycolyl glycerol (MMG) analogue demonstrated enhanced immunostimulatory activity in a dioctadecyl ammonium bromide (DDA)/Ag85B-ESAT-6 formulation. Elevated levels of IFN-γ and IL-6 were produced in spleen cells from mice immunised with a C32 MMG analogue comparable activity to the potent Th1 adjuvant, trehalose 6,6′-di-behenate (TDB).

Trehalose derivatives

A trehalose derivative of the formula: STR1 wherein one, two, three or four of R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from the group consisting o

An improved synthesis of trehalose 6-mono- and 6,6'-di-corynomycolates and related esters

A simplified synthesis of 6-mono- and 6,6'-di-corynomycolate esters of α,α-trehalose, and related compounds, was achieved by coupling the (hydroxyl-protected) acids to the partially trimethylsilylated sugar in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine.As acid reactants, (2-RS,3-RS)-3-hydroxy-2-tetradecyloctadecanoic acid (DL-corynomycolic acid) and its 2RS, 3SR diastereomer were prepared from methyl palmitate by sequential Claisen condensation, reduction, chromatographic separation, and saponification.Reaction with tert-butylchlorodimethylsilane (imidazole) gave the disubstituted ether-esters, which were converted into the required 3-tert-butyldimethylsilyl ethers by partial hydrolysis. 6-Linked monocorynomycolate was obtained in excellent yield (78percent) from the reaction of the RS,SR acid with the known heptakis-O-(trimethylsilyl)trehalose, and in good yield from equimolar portions of RS,RS acid and hexakis-O-(trimethylsilyl)trehalose.An excess (2.5-molar portions) of the RS,RS acid gave the 6,6'-diester (69percent).The mono- and di-palmitate were similarly obtained from (Me3Si)6-trehalose.The mono (RS,RS)-(Me3Si)6-trehalose coupling product was partially resolved on a silica gel column into its RR and SS diastereomers, the former corresponding to the naturally occurring trehalose monocorynomycolate.All coupling products were deprotected to free trehalose esters by treatment first with K2CO3 in methanol, then tetrabutylammonium fluoride-trifluoracetic acid in oxolane.

REGIO- AND DIASTEREOSELECTIVE ALDOL REACTION OF 1,2-CYCLOHEXANEDIONE DIANIONS WITH ALDEHYDES

The aldol reaction of 1,2-cyclohexanedione dianions with various aldehydes afforded threo and erythro aldols in a ratio of 82:18->99:1 in 60-85percent yields.A diastereoselective synthesis of racemic corynomycolic acid was achieved by using the reaction.

Method for treating and preventing bacterial infections

A method for treating and preventing bacterial infections which comprises administering a 6-O-acylmuramyl depeptide of the formula: STR1 wherein X represents a divalent residual group of an amino acid such as L-alanine, L-serine, L-valine, etc., Y represents a residual group of a middle to higher fatty acid having 10 to 60 carbon atoms and isoGln represents a residual group of isoglutamine, or a pharmaceutical composition containing a 6-O-acylmuramyl dipeptide of the formula(I) as an active ingredient to a patient afflicted therewith.