3-(tert-Butyldimethylsilyloxy)glutaric anhydride

Base Information

• Chemical Name: 3-(tert-Butyldimethylsilyloxy)glutaric anhydride
• CAS No.: 91424-40-7
• Molecular Formula: C11H20O4Si
• Molecular Weight: 244.363
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40399829
• Nikkaji Number: J643.422C
• Wikidata: Q72503011
• Mol file: 91424-40-7.mol

Synonyms:3-(TBDS)GA;3-(tert-butyldimethylsiloxy)glutaric anhydride

Chemical Property of 3-(tert-Butyldimethylsilyloxy)glutaric anhydride

Chemical Property:

• Appearance/Colour: White Sheet Crystalline Powder
• Vapor Pressure: 0.000993mmHg at 25°C
• Melting Point: 79-81 °C(lit.)
• Refractive Index: 1.451
• Boiling Point: 302.4 °C at 760 mmHg
• Flash Point: 113.6 °C
• PSA: 52.60000
• Density: 1.03 g/cm³
• LogP: 2.24040
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 244.11308565
• Heavy Atom Count: 16
• Complexity: 288

Purity/Quality:

99% ^*data from raw suppliers

3-(tert-Butyldimethylsilyloxy)glutaric anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(=O)OC(=O)C1
• Uses: 3-(tert-Butyldimethylsilyloxy)glutaric anhydride was employed as starting material for the preparation of labeling reagents.

Technology Process of 3-(tert-Butyldimethylsilyloxy)glutaric anhydride

There total 10 articles about 3-(tert-Butyldimethylsilyloxy)glutaric anhydride 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%

3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid (113794-48-2) → 3-(tert-butyldimethylsilyloxy)glutaric anhydride (91424-40-7)

Guidance literature:

With acetic anhydride; at 130 - 135 ℃; for 2 - 3h;

Reference yield: 89.7%

tert-butyldimethylsilyl chloride (18162-48-6) + dihydro-4-hydroxy-2H-pyran-2,6(3H)-dione (152294-14-9) → 3-(tert-butyldimethylsilyloxy)glutaric anhydride (91424-40-7)

Guidance literature:

With 1H-imidazole; In chloroform; at 20 - 30 ℃; for 24h; Inert atmosphere;

DOI:10.14233/ajchem.2014.16861

Reference yield: 80.0%

3-tert-butyldisilylglutarate → 3-(tert-butyldimethylsilyloxy)glutaric anhydride (91424-40-7)

Guidance literature:

With acetic anhydride; Reflux;

upstream raw materials:

3-[[(1,1-Dimethylethyl)dimethylsilyl]-oxy]pentanedioic acid,diethyl ester

3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid

diethyl 3-hydroxyglutarate

tert-butyldimethylsilyl chloride

Downstream raw materials:

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid methyl ester (S)-1-phenyl-ethyl ester

(3S,1'S)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate

3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid bis-((R)-1-phenyl-ethyl) ester

(3R,1'R)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate

Refernces

• 1、 -. "Preparation method of high-purity statin drug intermediate". . . Retrieved 2017/09/01.
• 2、 Jiang,Wang. "Synthesis of 3-[(tert-Butyldimethylsilyl)oxy]glutaric anhydride from citric acid". . p. 7867 - 7868. Retrieved 2015/02/02.