3,6,9,12,15-Pentaoxaoctadec-17-yn-1-ol

 CAS No.: 1036204-60-0  Cat No.: BP-500280  Purity: >95%  HNMR 4.5  

3,6,9,12,15-Pentaoxaoctadec-17-yn-1-ol is a polyethylene glycol-like ether linker featuring five internal ether oxygen atoms and a terminal propargyl alcohol motif, connected through a long, flexible aliphatic chain that terminates in an alkyne. The combination of multiple ether units provides conformational flexibility and aqueous compatibility, which can help preserve productive ternary-complex formation in PROTAC constructs by reducing steric penalties near the binding pharmacophores. The terminal alkyne enables bioorthogonal “click” conjugation strategies (e.g., CuAAC or related alkyne–azide coupling) to attach this linker to azide-functionalized warheads or E3 ligase ligands under mild conditions. As a result, it is a useful modular component for assembling PROTACs and related targeted degradation probes, allowing researchers to systematically vary linker length and polarity while maintaining a defined attachment handle for controlled synthesis and subsequent structure–activity studies.

3,6,9,12,15-Pentaoxaoctadec-17-yn-1-ol

Structure of 1036204-60-0

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Category
PROTAC Linker
Molecular Formula
C13H24O6
Molecular Weight
276.33
Related CAS
32199-97-6 (polymer)
Appearance
Pale Yellow Oily Liquid

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

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Popular Publications Citing BOC Sciences Products
Purity
>95%
Solubility
Soluble in DCM, DMF, DMSO
Appearance
Pale Yellow Oily Liquid
Application
Applicated in medical research, drug-release, nanotechnology and new materials research, cell culture. In the study of ligand, polypeptide synthesis support, a graft polymer compounds, new materials, and polyethylene glycol-modified functional coatings and other aspects of the active compound.<br />Alkyne-PEG5-OH (Propargyl-PEG5-alcohol) is a PEG derivative containing a hydroxyl group and a propargyl group. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The propargyl group can be reacted with azide-bearing compounds or biomolecules via copper catalyzed azide-alkyne Click Chemistry to yield a stable triazole linkage.
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]ethanol
Synonyms
Propargyl-PEG5-OH; Propargyl-PEG6-alcohol; Propyne-PEG5-OH; Alkyne-PEG5-OH; 2-[2-[2-[2-[2-(Propargyloxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol
Boiling Point
368.1±37.0 °C at 760 mmHg
Density
1.078±0.06 g/cm3 (Predicted)
InChI Key
IDULHQAZDNBPID-UHFFFAOYSA-N
InChI
InChI=1S/C13H24O6/c1-2-4-15-6-8-17-10-12-19-13-11-18-9-7-16-5-3-14/h1,14H,3-13H2
SMILES
C#CCOCCOCCOCCOCCOCCO
1. (Pyridino-15-crown-5-κN,O,O',O'',O''')bis-(thio-cyanato-κN)manganese(II)
Chengjuan Li, Zejing Feng, Dacheng Li, Daqi Wang Acta Crystallogr Sect E Struct Rep Online. 2008 Mar 14;64(Pt 4):m557.doi: 10.1107/S160053680800679X.
The title complex, [Mn(NCS)(2)(C(13)H(19)NO(4))] {systematic name: [3,6,9,12-tetra-oxa-18-aza-bicyclo-[12.3.1]octa-cosa-14(18),15,17-triene-κ(5)N,O,O',O'',O''']bis-(thio-cyanato-κN)manganese(I-I)}, was obtained by the reaction of MnCl(2)·4H(2)O and NaSCN with pyridino-15-crown-5. The Mn(2+) center has a distorted penta-gonal bipyramidal coordination geometry, coordinated by four O atoms and one N atom of the pyridino-15-crown-5 mol-ecule, and by the N atoms of the two NCS(-) ligands.
2. LY3437943, a novel triple GIP, GLP-1, and glucagon receptor agonist in people with type 2 diabetes: a phase 1b, multicentre, double-blind, placebo-controlled, randomised, multiple-ascending dose trial
Shweta Urva, Tamer Coskun, Mei Teng Loh, Yu Du, Melissa K Thomas, Sirel Gurbuz, Axel Haupt, Charles T Benson, Martha Hernandez-Illas, David A D'Alessio, Zvonko Milicevic Clinical TrialLancet. 2022 Nov 26;400(10366):1869-1881.doi: 10.1016/S0140-6736(22)02033-5.Epub 2022 Oct 27.
Background:Treating hyperglycaemia and obesity in individuals with type 2 diabetes using multi-receptor agonists can improve short-term and long-term outcomes. LY3437943 is a single peptide with agonist activity for glucagon, glucose-dependent insulinotropic polypeptide (GIP), and glucagon-like peptide 1 (GLP-1) receptors that is currently in development for the treatment of type 2 diabetes and for the treatment of obesity and associated comorbidities. We investigated the safety, pharmacokinetics, and pharmacodynamics of multiple weekly doses of LY3437943 in people with type 2 diabetes in a 12-week study.
3. [μ-6,9-Bis(carboxylatomethyl)-3,12-bis(car-boxymethyl)-3,6,9,12-tetraaza-tetradecanedioato]bis-[aqua-cobalt(II)] tetra-hydrate
Qi-Feng Qian, Jin-Hui Wu, Jin-Liang Qian Acta Crystallogr Sect E Struct Rep Online. 2013 Feb 1;69(Pt 2):m97.doi: 10.1107/S1600536813000196.Epub 2013 Jan 12.
The binuclear title complex, [Co(2)(C(18)H(26)N(4)O(12))(H(2)O)(2)]·4H(2)O, lies about a centre of inversion, the Co(II) atom being coordinated in a distorted octa-hedral arrangement defined by one water mol-ecule and N(2)O(3) donors derived from one end of a 6,9-bis(carboxylatomethyl)-3,12-bis(car-boxy-methyl)-3,6,9,12-tetraaza-tetradecanedioate (H(2)TTHA(4-)) tetra-anion. In the crystal, numerous O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

3,6,9,12,15-Pentaoxaoctadec-17-yn-1-ol, is designed to provide a flexible polyethylene glycol–like spacer combined with a terminal propargyl alcohol handle. Its ether-rich backbone can enhance solubility and reduce nonspecific interactions, while the alkyne enables efficient, orthogonal conjugation strategies commonly used in PROTAC assembly. The following sections describe the linker’s structure and practical reactivity considerations in detail.

Structure: The molecule contains multiple ether linkages forming an extended, flexible polyether chain, terminating in an alkynyl alcohol. Its connectivity includes a carbon–carbon triple bond and a primary alcohol, along with ether oxygen atoms that support hydrogen bonding and improved aqueous compatibility.

Reactivity: The terminal propargyl alcohol can be functionalized for PROTAC construction via standard alcohol derivatization (e.g., to form activated intermediates) or by leveraging the alkyne for orthogonal coupling approaches used in bifunctional ligand assembly. Typical conditions employ inert atmospheres when needed, polar aprotic solvents for substitution chemistry, and base/acid catalysts selected to preserve the alkyne and ether stability during linker–ligand conjugation.

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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

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* Total Molecular Weight:
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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Historical Records: 2,5-dioxopyrrolidin-1-yl 1-(bicyclo[6.1.0]non-4-yn-9-yl)-3-oxo-2,7,10-trioxa-4-azatridecan-13-oate | (2S,4R)-1-[(2S)-2-[(1-cyanocyclopropanecarbonyl)amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[(1S)-3-(methylamino)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]-3-oxopropyl]pyrrolidine-2-carboxamide | 4,7,10,13,16,19,22,25-Octaoxaoctacosa-1,27-diyne | (2S,4R)-N-[(1S)-1-(4-bromophenyl)-3-(methylamino)-3-oxopropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-1,2-oxazol-5-yl)butanoyl]pyrrolidine-2-carboxamide | 4,7,10,13,16-Pentaoxanonadeca-1,18-diyne | SNIPER(ABL)-039 | DBCO-S-S-PEG3-biotin | TCO-PEG4-biotin | (2S,4R)-N-[(1S)-1-(4-chlorophenyl)-3-(methylamino)-3-oxopropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-1,2-oxazol-5-yl)butanoyl]pyrrolidine-2-carboxamide | (2S,4R)-1-[(2S)-2-acetamido-3,3-dimethylbutanoyl]-N-[(1S)-1-(4-tert-butylphenyl)ethyl]-4-hydroxypyrrolidine-2-carboxamide | 3,6,9,12,15-Pentaoxaoctadec-17-yn-1-ol

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