130955-37-2

Basic information

• Product Name: 2,5,8,11-Tetraoxatridecan-13-ol, methanesulfonate
• Synonyms: Methanesulfonic acid 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester;mPEG4-OMs;mPEG4tosylate;2,5,8,11-tetraoxatridecan-13-yl methanesulfonate
• CAS NO: 130955-37-2
• Molecular Formula: C10H22O7S
• Molecular Weight: 286.346
• Mol File: 130955-37-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2,5,8,11-Tetraoxatridecan-13-ol, methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5,8,11-Tetraoxatridecan-13-ol, methanesulfonate(130955-37-2)
• EPA Substance Registry System: 2,5,8,11-Tetraoxatridecan-13-ol, methanesulfonate(130955-37-2)

Safety Data

• Hazardous Substances Data: 130955-37-2(Hazardous Substances Data)

Usage

Description

2,5,8,11-Tetraoxatridecan-13-ol, methanesulfonate, also known as m-PEG5-Ms, is a PEG linker containing a mesyl group. The mesyl group serves as a good leaving group for nucleophilic substitution reactions, while the hydrophilic PEG spacer enhances solubility in aqueous media.

Uses

Used in Pharmaceutical Industry:
2,5,8,11-Tetraoxatridecan-13-ol, methanesulfonate is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its mesyl group facilitates nucleophilic substitution reactions, making it a versatile building block for the development of new drugs.
Used in Drug Delivery Systems:
In the field of drug delivery, 2,5,8,11-Tetraoxatridecan-13-ol, methanesulfonate is used as a component in the design of targeted drug delivery systems. The hydrophilic PEG spacer improves the solubility and stability of drug carriers in aqueous environments, enhancing the bioavailability and therapeutic efficacy of encapsulated drugs.
Used in Organic Synthesis:
2,5,8,11-Tetraoxatridecan-13-ol, methanesulfonate is utilized as a reagent in organic synthesis, particularly for the preparation of PEGylated compounds. The presence of the mesyl group allows for efficient nucleophilic substitution, enabling the formation of a wide range of PEGylated products with potential applications in various industries, such as pharmaceuticals, materials science, and biochemistry.

Upstream product

• 112-35-6 triethylene glucol monomethyl ether 
• 128660-97-9 2-(2-(2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethoxy)ethan-1-ol 
• 727986-31-4 2-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxy)tetrahydropyran 
• 74654-05-0 8-methoxy-1-(methylsulfonyl)oxy-3,6-dioxaoctane 
• 23783-42-8 tetraethylene glycol monomethyl ether 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 873848-07-8 3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid 
• 873848-25-0 carbonic acid 3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzyl ester 4-nitro-phenyl ester 
• 873848-09-0 3,5-Bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid (2S,3R,4R,5S,6R)-2-allyloxy-5-hydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 
• 873848-13-6 N-[4-((2S,3R,4S,5R,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxymethyl)-phenyl]-3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzamide 
• 873848-08-9 3,5-Bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 873848-12-5 N-[4-((2R,4aR,6S,7R,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxymethyl)-phenyl]-3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzamide 
• 873848-22-7 C₅₁H₆₅NO₁₉ 
• 873848-26-1 Carbonic acid (2R,3S,4R,5R,6S)-6-allyloxy-5-allyloxycarbonylamino-4-(4-azido-3-chloro-benzyloxy)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzyl ester 
• 873848-21-6 C₅₈H₆₉NO₁₉ 
• 873848-28-3 acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-{6-allyloxy-5-allyloxycarbonylamino-2-[3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzyloxycarbonyloxymethyl]-4-hydroxy-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-3-yl ester 
• 873848-14-7 C₆₁H₈₅Cl₃N₂O₂₆ 
• 873848-27-2 C₆₀H₈₅ClN₄O₂₈ 
• 873848-23-8 C₆₆H₈₃Cl₃N₂O₂₈ 
• 720681-04-9 [3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-phenyl]-methanol 

Relevant articles and documents

Self-Assembly Can Direct Dynamic Covalent Bond Formation toward Diversity or Specificity

With the advent of reversible covalent chemistry the study of the interplay between covalent bond formation and noncovalent interactions has become increasingly relevant. Here we report that the interplay between reversible disulfide chemistry and self-assembly can give rise either to molecular diversity, i.e., the emergence of a unprecedentedly large range of macrocycles or to molecular specificity, i.e., the autocatalytic emergence of a single species. The two phenomena are the result of two different modes of self-assembly, demonstrating that control over self-assembly pathways can enable control over covalent bond formation.

GLUCOSE UPTAKE INHIBITORS AND USES THEREOF

The present invention relates to novel compounds that modulate cellular glucose uptake by affecting various targets, including, but not limited to those related to glycolysis and known transporters/co-transporters of the GLUT family. The compounds according to the invention are useful for treating cancer such as: neuroendrocrine neoplasms, gastrointestinal stromal tumors (GIST), renal cell carcinoma, paraganglioma, pheochromocytoma, pituitary adenoma, colorectal cancer, lung cancer, gastric cancer, pancreatic cancer sarcoma, head and neck cancer, melanoma, ovarian cancer and other cancers that rely on high levels of glycolysis for survival and proliferation; as well as in treating of autoimmune diseases, inflammation, infectious diseases, and metabolic diseases.

Site-Selective Modification of Peptides and Proteins via Interception of Free-Radical-Mediated Dechalcogenation

The development of site-selective chemistry targeting the canonical amino acids enables the controlled installation of desired functionalities into native peptides and proteins. Such techniques facilitate the development of polypeptide conjugates to advance therapeutics, diagnostics, and fundamental science. We report a versatile and selective method to functionalize peptides and proteins through free-radical-mediated dechalcogenation. By exploiting phosphine-induced homolysis of the C?Se and C?S bonds of selenocysteine and cysteine, respectively, we demonstrate the site-selective installation of groups appended to a persistent radical trap. The reaction is rapid, operationally simple, and chemoselective. The resulting aminooxy linker is stable under a variety of conditions and selectively cleavable in the presence of a low-oxidation-state transition metal. We have explored the full scope of this reaction using complex peptide systems and a recombinantly expressed protein.