116754-58-6

Usage

Uses

Used in Pharmaceutical Industry:
13-Bromo-1-tridecanol is used as a synthetic intermediate for the production of quinol fatty alcohols (QFA), which exhibit potent activity in promoting axonal growth. This makes it a valuable compound in the development of treatments for neurological disorders and injuries where axonal regeneration is crucial for recovery.
Used in Chemical Synthesis:
13-Bromo-1-tridecanol is used as a key building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure allows for selective functionalization and modification, making it a valuable asset in the development of new and innovative products.

InChI:InChI=1/C13H27BrO/c14-12-10-8-6-4-2-1-3-5-7-9-11-13-15/h15H,1-13H2

Upstream product

• 13362-52-2 1,13-tridecanediol 
• 16339-75-6 12-tridecenyl alcohol 
• 116452-11-0 2-(13-Bromo-tridec-2-ynyloxy)-tetrahydro-pyran 
• 80982-86-1 methyl ω-bromotridecanoate 
• 505-52-2 brassylic acid 
• 1472-87-3 dimethyl 1,11-undecanedicarboxylate 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 70326-40-8 11-bromoundecan-1-al 
• 4101-68-2 1,10-dibromodecane 
• 105-95-3 1,4-dioxa-cycloheptadecane-5,17-dione 
• 151277-05-3 (E)-13-Bromo-tridec-2-enoic acid methyl ester 

Downstream Products

• 4617-33-8 15-hydroxylpentadecanoic acid 
• 15462-16-5 13-bromotridecanoic acid 
• 338389-14-3 1-(14-hydroxytetradecyl-1-phenylsulfonyl)-2,6,6-trimethyl-1-cyclohexene 
• 887604-02-6 (((13-bromotridecyl)oxy)methyl)benzene 
• 887604-25-3 15-(2,5-dimethoxyphenyl)pentadecan-1-ol 
• 887604-05-9 ((pentadec-14-yn-1-yloxy)methyl)benzene 
• 903577-47-9 2-(15-Hydroxypentadecyl)benzene-1,4-diol 
• 887604-30-0 Q₃FA₁₅ 
• 887604-10-6 2-(15-Benzyloxy-pentadec-1-ynyl)-1,4-dimethoxy-benzene 
• 887604-15-1 1-(15-Benzyloxy-pentadec-1-ynyl)-2,4,5-trimethoxy-benzene 
• 887604-20-8 1-(15-Benzyloxy-pentadec-1-ynyl)-2,3,4,5-tetramethoxy-benzene 
• 411218-11-6 14-[1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-tetradecan-1-ol 
• 651331-73-6 14-[5-methoxy-1-(4-methoxybenzsulfonyl)-1H-indole-3-yl]-tetradecane-1-ol 
• 651331-69-0 14-[4-methoxy-1-(4-methoxybenzsulfonyl)-1H-indole-3-yl]-tetradecane-1-ol 

Relevant academic research and scientific papers

A Synthetic Route to the MT1-MMP Inhibitor Ancorinoside D

A methyl ester of ancorinoside D, a 3-acyltetramic acid metabolite of a sponge Penares sollasi, was synthesised in ten steps starting from a protected β- d -glucopyranosyl-(1→4)- d -galactopyranosyltrichloroacetimidate donor. Its attachment to the left half of the 3-acyl spacer by a Schmidt glycosylation, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated oxidation to the uronic acid, introduction of the Z -alkene via Wittig reaction, and functionalisation of the spacer terminus with Meldrum's acid gave a β-keto ester that reacted with dimethyl N -methyl- d -aspartate under neutral conditions to afford a fully protected ancorinoside D as the product of an unusual domino N -acylation-Dieckmann condensation. Global deprotection left a methyl ester of ancorinoside D, which resisted all saponification attempts.

Synthesis of 13C-labelled ω-hydroxy carboxylic acids of the general formula HO213C-(CH2)n-CH2OH or HO2C-(CH2)n-13CH2OH (n = 12, 16, 20, 28)

13C-labelled ω-hydroxy-carboxylic acids HO213C-(CH2)n-CH2OH or HO2C-(CH2)n-13CH2OH (n = 12, 16, 20, 28) with 13C labels selectively introduced either at the carboxy group or at the primary alcohol function at the end of the hydrocarbon chain have been synthesized. Different synthetic strategies had to be applied depending on the position of the label, the chain length of the respective synthetic target and due to economic considerations. 13C labels in general were introduced by nucleophilic substitution of a suitable leaving group with labelled potassium cyanide and subsequent hydrolysis of the nitriles to produce the corresponding labelled carboxy functions, which may also be reduced to give the labelled primary alcohol group. All new compounds are characterized by GC/MS, IR and NMR methods as well as by elemental analysis.

Method for synthesizing Micromelalopha troglodyta sex pheromone active ingredient

The invention relates to the technical field of insect sex pheromone component synthesis, and provides a novel method for synthesizing Micromelalopha troglodyta sex pheromone active ingredient. According to the novel method, 1, 13-tridecanol is used as an

Micromelalopha troglodyta sex pheromone attractant composition, lure and preparation method and application thereof

The invention relates to the technical field of pest attractants, and provides a Micromelalopha troglodyta sex pheromone attractant composition, a lure and a preparation method and application thereof. The attractant composition comprises Micromelalopha t

METABOLICALLY STABLE PRODRUGS

Provided are prodrugs of various therapeutic agents that provide enhanced bioavilabilty of the therapeutic agent, and methods of treatment conditions in a subject by administration of the one or prodrugs. As provided herein a prodrug includes a therapeutic agent covalently attached to a cap, the cap having a structure according to formula (I) where: R1 is a branched or linear substituted or unsubstituted C2-C6 alkyl, alkenyl, or alkynl; X is -S(0)2-; R2 is a branched or linear substituted or unsubstituted C4-C20 alkyl, alkenyl, or alkynyl; and R3 is -H, C3-C5 cycloalkyl, C3-C5 cycloheteroalkyl, -C(CH3)3, -CF3, -C(CF3)3, or a substituted or unsubstituted phenyl.

Chemical synthesis of diglucosyl diacylglycerols utilizing glycosyl donors with stereodirecting cyclic silyl protective groups

Chemical syntheses of the bacterial diglucosyl diacylglycerols 1-heptadecanoyl-2-pentadecanoyl-3-O-[6-O-(β-d-glucopyranosyl)-β-d-glucopyranosyl]-sn-glycerol and 1-(cis-13-octadecenoyl)-2-palmitoyl-3-O-[2-O-(α-d-glucopyranosyl)-α-d-glucopyranosyl]-sn-glycerol are described. The syntheses feature the stereoselective construction of glycosidic linkages in glycosylation reaction by utilizing glycosyl donors with stereodirecting cyclic silyl protective groups. The 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl (TIPDS) group was used for formation of the β-glycosidic linkage, while the di-tert-butylsilylene (DTBS) group was used for α-linkage formation. The silyl protective groups were chemoselectively cleavable without affecting acyl functionalities on the glycerol moiety and proved effective for the synthesis of diacylglycoglycerolipids.

Synthesis of ceramides NS and NP with perdeuterated and specifically ω deuterated N-acyl residues

The synthesis of 12 deuterated ceramides with either a deuteration at the last carbon atom of the amide bound fatty acid or a perdeuterated fatty acid chain is described. The ceramides were prepared starting from sphingosine or phytosphingosine and ω deuterated or perdeuterated fatty acids with PyBOP as activating agent in high yields. For the synthesis of the specifically deuterated fatty acids, dicarboxylic acids were transformed into ω deuterated alkyl bromide, which was chain elongated with blocked ω bromo alcohols by copper catalyzed Grignard coupling. Oxidation of regenerated alcohol function yields the ω deuterated fatty acids.

Viscosalines B1,2 and E1,2: Challenging new 3-alkyl pyridinium alkaloids from the marine sponge Haliclona viscosa

Four new 3-alkyl pyridinium alkaloids, the viscosalines B1 (1 a), B2 (1 b), E1 (2 a), and E2 (2 b), were isolated from the Arctic sponge Haliclona viscosa. The structure elucidation of these isomeric compounds was challenging due to ambiguous fragments that derive during "standard" mass spectrometric fragmentation experiments. The final structure elucidation relied on the use of a combination of synthesis, liquid chromatography, and mass spectrometry. Three different mass spectrometers were used to differentiate between the synthetic structural isomers: a time-of-flight (TOF) mass spectrometer and two ion-trap mass spectrometers with different ion-transfer technologies (i.e., skimmer versus funnel optics). Although at first none of the spectrometers returned spectra that permitted structure elucidation, all three mass spectrometers provided analysis that successfully differentiated between the isomers after thorough method optimization. The use of in-source collision-induced dissociation (CID) with the ion trap and TOF instrument returned the most interesting results. The mode of fragmentation of the viscosalines under different experimental conditions is described herein. After successful optimization of the mass spectrometric method applied, the chromatographic method was improved to distinguish the previously inseparable isomers. Finally, both the liquid chromatography and mass spectrometric methods were applied to the natural products and the results compared to those from the synthetic compounds. Copyright

General synthesis and aggregation behaviour of a series of single-chain 1,ω-Bis(phosphocholines)

The synthesis and physicochemical characterisation of a series of polymethylene-1,ω-bis(phosphocholines) with even-numbered chain lengths between 22 and 32 carbon atoms is described. Two new synthetic strategies for the preparation of long-chain 1,ω-diols as hydrocarbon building blocks are presented. The temperature-dependent self-assembly of the single-chain bolaamphiphiles was investigated by cryo transmission electron microscopy (cryo-TEM), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR).

Synthesis and mass spectrometric analysis of cyclostellettamines H, I, K and L

Very recently the new cyclostellettamines H, I, K and L were identified from a Brazilian sponge of the genus Pachychalina. They were isolated together with the known cyclostellettamines A-G in a mixture of only 1.5 mg. To obtain further material for biological investigations, the synthesis of the four new cyclostellettamines has been carried out. Since mass spectrometry plays an essential role in identifying these compounds a systematic analysis of the cyclostellettamines is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.