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14,14,14-Trifluoro-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate

14,14,14-Trifluoro-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate

Name: 14,14,14-Trifluoro-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1872433-61-8

Cat No.: BP-501177

Purity: ≥95% 4.5

14,14,14-Trifluoro-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate is a sulfonate-terminated, ether-rich PROTAC linker designed to provide a flexible polyethylene glycol–like segment while incorporating a terminal sulfonate leaving group for efficient conjugation. The tetraoxatetradecyl scaffold contains multiple oxygen atoms that can enhance solubility and modulate linker conformation, while the trifluoromethyl substitution contributes to chemical stability and can influence physicochemical properties relevant to cellular experiments. In PROTAC construction, this type of linker is typically used to connect a target-binding ligand to an E3 ligase recruiter through nucleophilic substitution or related coupling at the sulfonate terminus, enabling formation of a stable, well-positioned ternary complex. Its ether content and defined chain length help tune the spatial relationship between binding domains, often improving degradation efficiency and selectivity in targeted protein degradation studies.

Structure of 1872433-61-8

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PROTAC Linker

Molecular Formula

C17H25F3O7S

Molecular Weight

430.44

Appearance

Pale Yellow Oily Matter

* For research and manufacturing use only. Not for human or clinical use.

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Purity

≥95%

Solubility

Soluble in DMSO

Appearance

Pale Yellow Oily Matter

Storage

Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

2-[2-[2-[2-(2,2,2-trifluoroethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate

Synonyms

1,1,1-Trifluoroethyl-PEG5-Tos; 1,1,1-Trifluoroethyl-PEG4-Tos; 14,14,14-Trifluoro-3,6,9,12-tetraoxatetradec-1-yl 4-methylbenzenesulfonate; 3,6,9,12-Tetraoxatetradecan-1-ol, 14,14,14-trifluoro-, 4-methylbenzenesulfonate

Boiling Point

495.8±45.0°C at 760 mmHg

Density

1.3±0.1 g/cm3

InChI Key

UYAXEKCLHRTXQU-UHFFFAOYSA-N

InChI

InChI=1S/C17H25F3O7S/c1-15-2-4-16(5-3-15)28(21,22)27-13-12-25-9-8-23-6-7-24-10-11-26-14-17(18,19)20/h2-5H,6-14H2,1H3

SMILES

CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCOCC(F)(F)F

1. Discovery of a tetracyclic quinoxaline derivative as a potent and orally active multifunctional drug candidate for the treatment of neuropsychiatric and neurological disorders

Peng Li, Qiang Zhang, Albert J Robichaud, Taekyu Lee, John Tomesch, Wei Yao, J David Beard, Gretchen L Snyder, Hongwen Zhu, Youyi Peng, Joseph P Hendrick, Kimberly E Vanover, Robert E Davis, Sharon Mates, Lawrence P Wennogle Multicenter StudyJ Med Chem. 2014 Mar 27;57(6):2670-82.doi: 10.1021/jm401958n.Epub 2014 Mar 5.

We report the synthesis and structure-activity relationships of a class of tetracyclic butyrophenones that exhibit potent binding affinities to serotonin 5-HT(2A) and dopamine D2 receptors. This work has led to the discovery of 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8-yl)-1-(4-fluorophenyl)-butan-1-one 4-methylbenzenesulfonate (ITI-007), which is a potent 5-HT(2A) antagonist, postsynaptic D2 antagonist, and inhibitor of serotonin transporter. This multifunctional drug candidate is orally bioavailable and exhibits good antipsychotic efficacy in vivo. Currently, this investigational new drug is under clinical development for the treatment of neuropsychiatric and neurological disorders.

2. An Improved Scalable Synthesis of the Potent Antiviral (S)-HPMPA

Racherla Kishore Kumar, Yogesh S Sanghvi, Paidi Yella Reddy, Shyamapada Banerjee Curr Protoc. 2022 Nov;2(11):e602.doi: 10.1002/cpz1.602.

We present an improved synthesis of (S)-HPMPA (1) from an easily accessible and commercially available compound, (S)-3-(benzyloxy)propane-1,2-diol (10). Tritylation of primary alcohol 10 was highly selective, and pure product was isolated in good yield. Alkylation of (R)-1-(benzyloxy)-3-(trityloxy)propan-2-ol (11) with diethyl p-toluenesulfonyloxymethyl phosphonate (6) using sodium hydride in tetrahydrofuran followed by detritylation afforded the desired chiral synthon 12. Tosylation of the primary alcohol and subsequent reaction with sodium adeninate afforded protected S-HPMPA (14). Global deprotection using concentrated hydrochloric acid in a sealed tube afforded S-HPMA (1), and the deprotected 1 was crystallized from water and acetone to obtain a 99% pure product. © 2022 Wiley Periodicals LLC. Basic Protocol 1: Preparation of (R)-1-(benzyloxy)-3-(trityloxy)propan-2-ol (11) Basic Protocol 2: Preparation of diethyl (S)-(((1-(benzyloxy)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate (12) Basic Protocol 3: Preparation of (R)-3-(benzyloxy)-2-((diethoxyphosphoryl)methoxy)propyl-4-methylbenzenesulfonate (13) Basic Protocol 4: Preparation of diethyl (S)-(((1-(6-amino-9H-purin-9-yl)-3-(benzyloxy)propan-2-yl)oxy)methyl)phosphonate (14) Support Protocol 1: Preparation of sodium adeninate Basic Protocol 5: Preparation of (S)-(((1-(6-amino-9H-purin-9-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonic acid (1).

3. 2-Ammonio-5-chloro-4-methylbenzenesulfonate, its 1-methyl-2-pyrrolidone and dimethyl sulfoxide monosolvates and a corrected structure of 2,2'-(1,4-phenylene)di(4,5-dihydroimidazolium) bis(4-aminobenzenesulfonate) dihydrate

Sándor L Bekö, Jan W Bats, Martin U Schmidt Acta Crystallogr C. 2012 Feb;68(Pt 2):o45-50.doi: 10.1107/S0108270111054205.Epub 2012 Jan 6.

2-Ammonio-5-chloro-4-methylbenzenesulfonate, C(7)H(8)ClNO(3)S, (Ia), is an intermediate in the synthesis of lake red azo pigments. The present structure determination from single-crystal data confirms the results of a previous powder diffraction determination [Bekö, Thoms, Brüning, Alig, van de Streek, Lakatos, Glaubitz & Schmidt (2010). Z. Kristallogr. 225, 382-387]. The zwitterionic tautomeric form is confirmed. During a polymorph screening, two additional pseudopolymorphs were obtained, viz. 2-ammonio-5-chloro-4-methylbenzenesulfonate 1-methyl-2-pyrrolidone monosolvate, C(7)H(8)ClNO(3)S·C(5)H(9)NO, (Ib), and 2-ammonio-5-chloro-4-methylbenzenesulfonate dimethyl sulfoxide monosolvate, C(7)H(8)ClNO(3)S·C(2)H(6)OS, (Ic). The molecules of (Ib) have crystallographic m symmetry. The 1-methyl-2-pyrrolidone solvent molecule has an envelope conformation and is disordered around the mirror plane. The structure shows hydrogen-bonded ladders of molecules [graph-set notation C(2)(2)(6)R(2)(2)(12)] in the [010] direction. The benzene groups of adjacent ladders are also stacked in this direction. A different type of hydrogen-bonded ladder [graph-set notation C(6)R(2)(2)(4)R(4)(4)(12)] occurs in (Ic). In (Ia), (Ib) and (Ic), the molecules correspond to the zwitterionic tautomer. The structure of the cocrystal of 4-aminobenzenesulfonic acid with 1,4-bis(4,5-dihydroimidazol-2-yl)benzene [Shang, Ren, Wang, Lu & Yang (2009). Acta Cryst. E65, o2221-o2222] is corrected; it actually contains 4-aminobenzenesulfonate anions and 2,2'-(1,4-phenylene)di(dihydroimidazolium) dications, i.e. 2,2'-(1,4-phenylene)di(4,5-dihydroimidazolium) bis(4-aminobenzenesulfonate) dihydrate, C(12)H(16)N(4)(2+)·2C(6)H(6)NO(3)S(-)·2H(2)O. Hence, all known structures of aminobenzenesulfonic acid complexes contain ionic or zwitterionic molecules; there is no known structure with a neutral aminobenzenesulfonic acid molecule.

This PROTAC linker is designed to provide a chemically robust, ether-rich spacer that can be used to connect protein-binding ligands to achieve controlled proximity-driven degradation. Its trifluorinated and polyether character supports favorable stability and solubility behavior commonly beneficial in linker-mediated conjugation workflows. The molecule will be described in detail below, including its structure-related features and practical reactivity considerations for assembling PROTAC constructs.

Structure: The linker comprises a long, polyether (tetraoxatetradecyl) chain featuring multiple ether linkages and a terminal sulfonate ester derived from 4-methylbenzenesulfonic acid. A trifluorinated segment contributes to electronic modulation, while the sulfonate provides a leaving group for subsequent functionalization.

Reactivity: As a sulfonate ester, it is suitable for nucleophile-driven substitution reactions that enable installation of PROTAC attachment points. Linker coupling is typically performed under conditions that preserve sulfonate reactivity while minimizing side reactions, using appropriate nucleophiles (for example, amines or alcohol/thiol-derived nucleophiles) in polar organic solvents. Reaction progress is monitored by standard analytical methods, and mild base or acid–base buffering is selected to balance nucleophile strength and linker stability.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂