CAS 2514946-87-1

N-((1E,3E,5R,6R,9E,11Z,13E,14aS,16S,18aR)-6-((2R,3S,4R)-4-acetamido-3-hydroxypentan-2-yl)-2,5,12,14a-tetramethyl-8-oxo-5,8,14a,15,16,18a-hexahydro-6H-benzo[h][1]oxacyclohexadecin-16-yl)oct-7-ynamide

Other Click Chemistry Reagents

About This Compound

This category encompasses diverse reagents used across various click chemistry reactions, including activated esters, Michael acceptors, epoxides, and multi-functional building blocks. These compounds participate in thiol-ene reactions, Michael additions, ring-opening reactions, and other modular coupling strategies that meet the criteria of click chemistry — high yield, wide scope, simple conditions, and easy purification.

Molecular FormulaC12H15NO4 Molecular Weight237.255 g/mol InChIKeyGMBVDHZUSCRQGM-UHFFFAOYSA-N CAS Registry2514946-87-1 Literature Refs2 references

Synthesis Routes

Showing 2 of 2 available routes, sorted by yield.

Route 1

1 step Yield: 68%
2,5-dioxopyrrolidin-1-yl oct-7-ynoate
CAS 2514946-87-1
C12H15NO4
+
N-((2R,3S,4R)-4-((1E,3E,5R,6R,9E,11Z,13E,14aS,16S,18aR)-16-acetamido-2,5,12,14a-tetramethyl-8-oxo-5,8,14a,15,16,18a-hexahydro-6H-benzo[h][1]oxacyclohexadecin-6-yl)-3-hydroxypentan-2-yl)acetamide
C32H46N2O5
N-((1E,3E,5R,6R,9E,11Z,13E,14aS,16S,18aR)-6-((2R,3S,4R)-4-acetamido-3-hydroxypentan-2-yl)-2,5,12,14a-tetramethyl-8-oxo-5,8,14a,15,16,18a-hexahydro-6H-benzo[h][1]oxacyclohexadecin-16-yl)oct-7-ynamide
Conditions With triethylamine In dichloromethane at 25℃; Inert atmosphere;
Reference Current Patent Assignee: THE UNIVERSITY OF IOWA - WO2025/231146, 2025, A1 Location in patent: Paragraph 0036; 0280-0283
Source Reaxys

Route 2

1 step Yield: 68%
2,5-dioxopyrrolidin-1-yl oct-7-ynoate
CAS 2514946-87-1
C12H15NO4
+
C30H44N2O4*C2HF3O2
C2HF3O2*C30H44N2O4
N-((1E,3E,5R,6R,9E,11Z,13E,14aS,16S,18aR)-6-((2R,3S,4R)-4-acetamido-3-hydroxypentan-2-yl)-2,5,12,14a-tetramethyl-8-oxo-5,8,14a,15,16,18a-hexahydro-6H-benzo[h][1]oxacyclohexadecin-16-yl)oct-7-ynamide
Conditions With triethylamine In dichloromethane at 25℃; Inert atmosphere;
Reference Qian, Shan; Qiu, Haibo; Sanchez, Phillip R.; Head, Sarah A.; Hartke, Ruth; Liu, Jun O.; Zheng, Wei; Jin, Zhendong [ACS Medicinal Chemistry Letters, 2026, vol. 17, # 6, p. 1416 - 1420] DOI
Source Reaxys

Related Compounds

Other Other Click Chemistry Reagents in our catalog:

Frequently Asked Questions

What defines a reaction as "click chemistry"?

According to Sharpless (2001), click reactions must be modular, wide in scope, high-yielding, generate only inoffensive byproducts, be stereospecific, and use readily available starting materials. They should proceed under simple conditions (ideally insensitive to oxygen and water), use benign solvents, and products should be easy to isolate without chromatography.

How do I choose the right click reaction for my application?

For in vitro bioconjugation: CuAAC is the gold standard. For live-cell work: use SPAAC or IEDDA (copper-free). For protein labeling: SuFEx or Staudinger ligation. For polymer chemistry: thiol-ene or thiol-Michael. For prodrug activation: click-to-release (IEDDA-based elimination). Consider reaction speed, biocompatibility, and orthogonality requirements.

Can click reactions be performed in aqueous media?

Most click reactions are compatible with aqueous conditions. CuAAC works in water/t-BuOH mixtures. SPAAC and IEDDA proceed rapidly in pure aqueous buffer. Thiol-ene reactions can be performed in water with water-soluble photoinitiators. SuFEx reactions work in organic/aqueous biphasic systems. This aqueous compatibility is one of the key advantages of click chemistry for biological applications.

How do I confirm click reaction completeness?

For CuAAC/SPAAC: disappearance of the azide stretch at ~2100 cm⁻¹ in IR spectroscopy. For IEDDA: loss of the tetrazine UV-Vis absorption (pink color fades). General methods: TLC, HPLC, ¹H NMR (triazole peak), and mass spectrometry. For bioconjugation: SDS-PAGE with fluorescent readout or western blot.

What is the typical shelf life of click chemistry reagents?

Azides: 6–12 months at −20 °C (avoid light). Terminal alkynes: 12+ months at −20 °C. Cyclooctynes (DIBO, DBCO, BCN): 6–12 months at −20 °C (light-sensitive). Tetrazines: 6–12 months at −20 °C (light and moisture sensitive). TCO derivatives: 3–6 months at −20 °C (isomerization-prone). Sulfonyl fluorides: 12+ months at room temperature.

Last updated: July 27, 2026