5-Carboxyfluorescein Dipivalate NHS Ester

Base Information

• Chemical Name: 5-Carboxyfluorescein Dipivalate NHS Ester
• CAS No.: 186032-65-5
• Molecular Formula: C₃₅H₃₁NO₁₁
• Molecular Weight: 641.631
• DSSTox Substance ID: DTXSID301104307
• Mol file: 186032-65-5.mol

Synonyms:186032-65-5;5-Carboxyfluorescein Dipivalate NHS Ester;5-CARBOXYFLUORESCEIN DIPIVALATE N-HYDROXYSUCCINIMIDE ESTER;(2,5-dioxopyrrolidin-1-yl) 3',6'-bis(2,2-dimethylpropanoyloxy)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylate;5-(((2,5-Dioxopyrrolidin-1-yl)oxy)carbonyl)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate);Spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylic acid, 3',6'-bis(2,2-dimethyl-1-oxopropoxy)-3-oxo-, 2,5-dioxo-1-pyrrolidinyl ester;SCHEMBL13237869;FACUWLWNJGISGM-UHFFFAOYSA-N;DTXSID301104307;AKOS015914657;5-Carboxyfluorescein dipivalate succinimide ester;2,5-Dioxo-1-pyrrolidinyl 3',6'-bis(2,2-dimethyl-1-oxopropoxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylate;5-((2,5-dioxopyrrolidin-1-yloxy)carbonyl)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate);Spiro[isobenzofuran-1(3H),9'-[9h]xanthene]-5-carboxylicacid,3',6'-bis(2,2-dimethyl-1-oxopropoxy)-3-oxo-,2,5-dioxo-1-pyrrolidinylester

Chemical Property of 5-Carboxyfluorescein Dipivalate NHS Ester

Chemical Property:

• PSA: 151.81000
• LogP: 5.31630
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 641.18971080
• Heavy Atom Count: 47
• Complexity: 1260

Purity/Quality:

99% ^*data from raw suppliers

5-CarboxyfluoresceinDipivalateN-HydroxysuccinimideEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OC1=CC2=C(C=C1)C3(C4=C(C=C(C=C4)C(=O)ON5C(=O)CCC5=O)C(=O)O3)C6=C(O2)C=C(C=C6)OC(=O)C(C)(C)C
• Uses: 5-Carboxyfluorescein Dipivalate N-Hydroxysuccinimide Ester is used as a probe in fluorescent dye labeled terminators for DNA sequencing.

Technology Process of 5-Carboxyfluorescein Dipivalate NHS Ester

There total 5 articles about 5-Carboxyfluorescein Dipivalate NHS Ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3',6'-bis(2,2-dimethyl-1-oxopropoxy)-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylic acid (144676-12-0) → 5-carboxyfluorescein dipivalate (186032-65-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 3h;

Reference yield:

5-carboxyfluoroscein (76823-03-5) → 5-carboxyfluorescein dipivalate (186032-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: DIPEA / dimethylformamide; various solvent(s) / 72 h / 20 °C

2: EDC / various solvent(s)

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; 1: Esterification / 2: Esterification;

DOI:10.1021/jo991449h

Reference yield:

2,2-dimethylpropanoic anhydride (1538-75-6) → 5-carboxyfluorescein dipivalate (186032-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: DIPEA / dimethylformamide; various solvent(s) / 72 h / 20 °C

2: EDC / various solvent(s)

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; 1: Esterification / 2: Esterification;

DOI:10.1021/jo991449h

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

3',6'-bis(2,2-dimethyl-1-oxopropoxy)-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylic acid

2,2-dimethylpropanoic anhydride

5-carboxyfluoroscein